Skip to main content

We're fighting for the future of our library in court. Show your support now!

Full text of "Parry’s Cyclopedia Of Perfumery; A Handbook On The Raw Materials Used By The Perfumer, Their Origin, Properties, Characters And Analysis; And On Other Subjects Of Theoretical And Scientific Interest To The User Of Perfume Materials, And To Those Who Have To Examine And Value Such Materials."

See other formats




, ORGANIC ]MEDIGAI\IENTS. Translated by 
i W. A. SiLViiSTHR, M.Sc. 22 Illustrations. 


, C.D.IL, F.I.C., and H. B. Stevi-ns, O.B.E., 
j i'.I.C. Tuvlfih Edition. 

1 R. WiiY.MPEii. Second Edition. 54 Illustra- 

i lions, 


1 TRY. By De. Ettore ]\Iolikaei. Second 
English Edition. Translated bv T. H. Pope, 

, B.Sc., F.I C.. A.C.G.I. 

Inoi'fianic. 330 Iliustmtion.^. 

Organic. Part 1 . 254 Illustrations. 

' Part II. 303 Illustrations. 


1 ANALYSIS. By F. Pregl, D.Sc., Pii.D. 

I Translated from and German Edition b}’’ E. 

FvLE:;.'iN, B.Sc., Fii.D. 42 Illustrations. 

EMULSIFICATION. By W. Cl.\yton, D.Sc., 
F.I.e. 22 Illustrations. 

ANALYSIS. New Edition (5th), Vols. 1 . — IX. 
Edited by S. S. S.adtler, S.B., E. C. 
L.ATHROP, A.B., Ph.D., and C. A. Mitchell, 
:\I.A., F.I.e. 

CHEhllSTRY. Translated b}' T. H. Pope, 
B.Sc., A.C.G.I. Vol. I. 58 Illustrations. 21s. 
Vol. II. 105 Illustrations. 




i OF 


On the Raw Materials used by the Perrumcr, their 
Origin,. Properties, Characters and Analysis ; and 
on other subjects of Theoretical and Scientific 
Interest to tiie User of Perfume Materials, and to 
those who have to Examine and Value such Materials 



B.Sc., F.I.C., F.C.S. 
Analytical and Consulting Chemist 

A — L 




P; lilted j}i Great Brifatii. 


The need for a scientific ivork of reference devoted to perfumerv 
and ds raw materials has long been felt, and it is hoped that the 

publication of the present volumes will go some way towards 
meeting that want. 

Tormulai for finished perfumes are not dealt vnth. In the first 
place, reaUy good formula! are rarely published, and the best of 
those that are are merely an index to the perfumer, giving him 
hmts as to the direction in which he should experiment. Wliere 
such formula! are required they will be found to a more or less 
unlimited extent in books of a more empirical character. 

^ I have to express my great indebtedness to the folloiving publica- 
tions and individuals for the kind way, in the case of the former 
ui winch they have aUou'cd me to use them vlth a free hand, and’ 
in the case of the latter, for so Idndly contributing articles which’ 
will be found over them respective initials 

The Perfumery and Essential Oil Record. 

The Chemist and Druggist. 

La Parfumerie Moderne. 

Les Parfums de Fraiice. 

Messrs. Roure-Bertrand Fils, Bulletin. 

Messrs. Schimmel & Co., Reports. 

C. T Boimett, B.So., P.I.O. (O.T.B .) ; M. Dowlmrst, 

w M-So., P.I.e. 



J JTT “taoyMge tto iindneas of Messrs. Scott, Greon- 

The Chemstry of Essential Oils and Artiflciaf Perfumes ” the 
copyright of which they own. , * 


56a, Gbeat Dover Street, 

London, S.E. 1. 

ABIES OILS. — ^The oils usualty known as pine needle oils 
include those obtained from various species of pinus, larix and 
abies. (See under “ Pine bfeedle Oil.”) 

ABSOLUTES. — ^The term “absolutes” is’ applied to the 
most' highly concentrated form of floral perfumes which can be 
made. There are numerous trade names for these highly-concen- 
trated preparations, but they are, in the main, identical with, or 
very similar to, the substances known commonly as absolutes. 
The extraction of the perfume material of the plant by means of 
a volatile solvent, which is afterwards recovered by distillation, 
was used, in a more or less experimental manner, about the year 
1835. Robiquet appears to be the earliest experimenter in this 
du’ection, but it was due to Massignon and to Naudin to make 
the process a commercial success. During the past tliirty years 
the extraction has been carried out on a commercial scale. The 
oily, waxy, and resinous matters of the plant are extracted from 
the plant substance by means of the volatile solvent, leaving 
behind the bulk of the inert and inodorous matter. The volatile 
solvent, such as petroleum ether, is recovered by distillation, 
generally under reduced pressure, in order to keep the temperature 
as low as possible. The solvent must be able to dissolve the whole 
of the odorous substances present, and must have no chemical 
action on them. It should also dissolve as little as possible of 
any inodorous substances. Eurther, it should boil at the lowest 
possible temperature and leave no odour beliind when evaporated. 
The semi-solid residue left behind on the evaporation of the 
solvent consists of the odorous constituents of the plant, together 
with the inodorous waxy matter. These substances are usually 
known as “ concretes.” They are either sold as such (when the 
perfumer has to filter ofi the matter insoluble in alcohol), or they 
are further treated and converted into absolutes. This is effected 
by treating them with alcohol in shaking machines, and the 
alcohol is filtered. It is then exposed to a very low temperature 
and dissolved wax is thus separated. The clear alcoholic solution 


i? now cither e^'aporated at a low temperature and the residue 
sold as a)i absolute, or the perfume material is isolated by 
salting out, when it can be separated, or it can be dissolved out 
from the alcohol mixed vith brine, hy petroleum other, which is 
then evaporated, and the residue is the absolute. 

An absolute i.s understood to be a pure vegetable imoduct free 
from the addition of synthetics, and it should form a clear 
solution with alcohol, which ought not to precipitate on 

The^ solvent in almost general use to-day is a highly-purified 
petroleum ether. >So far as any comparative figure can be given, 
it ma 3 * be said that the concretes arc about forty times as strong 
as the coiresponding pomades known as “ No. 3G,” and the 
absolutes stronger still. 

ACACIA.— This genus of the natural order LtguwwoscB 
includes a number of plants with sweet-scented flowers. The two 
of really cc mmerdal importance arc Acacia Farnesiana, which 
yields the cassic perfume, and Acacia dcalhala, which, with several 
other .species, \dclds the well-knomi mimosa perfume. 

A small quantity’ of perfume is obtained for local use in 
Austraha from various species of acacia known commonly as 
wattle blossoms. 

The perfume of the cassie flowers is veqy delicate, and is best 
dealt with in the form of a pomade, but it is also made as an 
absolute flower oil. It is wideN distributed over the warmer 
districts of all continents. Tor example,^ it is found in EgjqDt, 
Aiistralia, the Hawaiian Islands, the Philippine Islands, North 
and South America, Prance, Algeria, Sjnia, northern India, and 
New Caledonia. In Europe the collection of flowers commences 
when the plants are three j-ears old. Each tree jdelds about 
500 to GOO kg. of flowers, which are gathered twice weekly dui’ing 
the months of September, October, and November, and sometimes 
even in December. A good deal of pomade was at one time made 
in India, but to-daj’- very little is manufactured there. In Sjuria, 
near BajTCuth, the pomade is made, as the cassie tree is there 
very plentiful. In the south of Prance the plant flourishes best 
in the neighbourhood of Grasse and Cannes, vdierc it is knoum as 
” cassie ancienne or “ casillier de Parnese.” A less odorous 
species is Acacia cavenia, known as “ cassie romane.” 

The principal flowering season is October-November, whilst in 
favoura,ble seasons flowers are picked as late as January or- 
Pebruary. Essential oil of cassie, a somewhat rare product, has 



a specific gravity 1-040 to 1-058 ; refractive index, 1-5130 to 
1-5150 ; ester value, 114 to 230 ; and melts at about 18°. It 
contains farnesol, geraniol, linalol, benzaldebyde, eugenol, benzyl 
alcohol, methyl saHcylate, decylic aldehyde, cuminic aldehyde, 
anisic aldehyde, para-cresol, and a ketone of violet colour. 

The essential oil from Acacia cavenia contains eugenol, methyl 
salicylate, benzaldehyde, benzyl alcohol, anisic aldehyde, eugenol 
methyl ether, and a ketone with a violet odour. Linalol and 
decylic aldehyde are also probably present. 

Cassie, either in the form of a pomade, concrete, or absolute, is 
of great value in the preparation of violet bouquets. Synthetic 
cassie perfumes can be, and are, manufactmed on the basis of the 
composition of the essential oil given above, assisted by the 
judicious use of traces of the higher fatty aldehydes, especially the 
12 carbon aldehyde, a small quantity of one or other of the 
ionone ketones, and para-methyl acetophenone. 

Acacia dealbata {Mimosa dealbata) is the principal tree whose 
flowers are used for the preparation of the mimosa perfume, in 
the same way as the cassie perfume. The crop is gathered from 
February to March. Acacia fioribimda is also used for the perfume. 
Artificial mimosa resembles artificial cassie, and methyl-aceto- 
phenone and its homologues are used in its preparation, together 
with methyl-heptin-carbonate and hydroxycitronellal. 

The oil from Robinia pseudacacia is of good odour value, but is 
scarcely a commercial article. The flowers are sometimes made 
into a concrete or absolute flower oil, which has a typical acacia 
odour. The essential oil has a specific gravity 1-05, and contains 
linalol, a-terpineol, benzyl alcohol, indol, and heliotropin (Elze, 
Cham. Zeit., 34, 814). 

(For an account of other species, see Les Parfitmes de France, 
1924, 13, 35.) 

ACETEUGENOL. — ^This body, is a crystalline 

compound formed by the action of acetic anhydride on eugenol. 
It melts at 29°. It is present to a very small extent in oil of 

ACETIC ACID. — Solutions of acetic acid are employed in 
•the manufacture of toilet vinegars. It should be pure, water- 
white, and free from the slightest enipyreumatic odour. It is an 
acid obtained by the distillation of wood (also synthetically), and 
has the formula CHgOOOH. The following table gives the most 
useful strengths as determined by the specific gravity, which. 

P E P r V M E B Y 

wiicic u specific jiraviiy ovei’ 1*050 is being clefilt with, must be 
ciiecived by titration : — 

Sp. gr. 

Percent. | 

Sp. gr. 

Per cent. 



































' 1-066 








AGETIN. — The term acelin is used to include the three acetic 
esters of glvcerin. mono-, di-. and in- acetin. A mixture of these 
is used as an adulterant of essential oils, but, being much more 
soluble in water than the natural esters, may readity be detected 
bv washing two or three times witli hot water, and noting anj 
decrease in volume of the oil. The acetins are used to some 
extent as solvents for essential oils, either alone or in conjunction 
vith alcohol ; they are miscible iii all proportions with 20 under 
proof spirit. {Vide ‘'Artificial Esters.' ) 

ACETON APHTHONE .—This body, a-naphthyl-methyl ketone 
C10H7.CO.CH3, is prepared by condensing naphthalene and acetyl 
chloride with the assistance of aluminium chloride. It is best 
condensed in monochlor-benzene solution (Chopin, French patent 
530,257). It has a very useful orange-blossom odour, and is useful 
in admixture with phcnyl-etlnd alcohol and methyl anthranilate 
in the preparation of art.ificial neroli oils. It forms crystals 
melting at 34°, and boils at 295°. 

ACETOPHENONE.— This ketoire, CcH5.CO.CH3, occurs 
iiaturallj’’ in oil of ladanuin resin, and in the oil of an Australian 
plant, Slirlmgia laiifolia. of which it forms about 90 per cent. 

It has a persistent and powerful odour, which is taken advantage 
of by perfumers in the preparation of perfumes of the type of 
new-mown hay, s^sninga, and the lilce. 

It is prepared artificially by pouring acetyl chloride slowly on 
to a mixture of benzene and aluminium clrloride at a lov' tempera- 
ture. Hydrochloric acid is evolved, and the product is left for 
several hours at ice temperat'ure. It is then washed with water, 
then vith dilute advali, and rectified mi vacuo. Its oxime melts 
at 59°. 



Acetophenone is a crystalline substance melting at 19° to 20°, and 
boiling at 200° to 202°, It has a specific gravity 1-033, and refractive 
index 1-5355. It is used medicinally under the name “ Hypnone.” 

ACETYLATION. — See “ Alcohols, Determination of.” 

ACHASMA WALANG, OILS OF.— The essential oils have 
been extracted separately from the leaves, the stems, and the 
roots of this member of the Zingiber acece, Achasma Walang Val., 
or Amomum Walang Bl., which in’ Java goes under the name of 
daon walang. 

JRoiire-Bertrand Fils {Bulletin, April, 1914:, 154) give the follow- 
ing characters of the oils : — 

Oil of the Leaves (yield, 0-25 per cent.) 

Specific gravity .... ,0-850 

Acid value ..... 10-1 

Optical rotation . . . . —0° 34' 

Saponification value . . .70 

Aldehj^des (neutral sulphite method) . 97 per cent. 

Oil of the Steins (yield, 0-2 per cent.) 

Specific gravity . . . , 0-860 

Acid value ..... 26 

Optical rotation .... —0° 58' 

Saponification value . . .75-6 

Saponification value after acetylation 285-6 
Aldehydes 96 per cent. 

Oil of the Boots (yield, 0-15 per cent.) 

Specific gravity .... 0-856 

Acid value .’.... 18-9 

Optical rotation .... —0° 30' 

Saponification value ... 70 

Saponification value after acetylation 285-6 
Aldehydes 96 per cent. 

ACHILLEA M OS CHAT A. — ^This plant, known as the musk- 
scented milfoil, is found on the Alps at an elevation of 5,000 to 
10,000 feet. On distfilation of its flowers and leaves it yields an 
essential oil which has been used to perfume the Swiss liqueur 
known as Iva. It contains cineol, valeric aldehyde, Zceyo-camphor, 
palmitic acid, and an oxygenated body termed ivaol, of the 
formula C24H4o02- The pure oil has a specific gravity 0-928 
to 0-960 ; optical rotation, — 12° to — 15° ; refractive index, 
1-4760 ; and ester value, 18 to 44. 

ACOR.US CALAMUS. — ^This plant, commonly known as 
the sweet flag, is a member of a genus of semi-aquatic plants 


belonging to the natural order Aroidce. It must not be confounded 
with the Indian “ calamus aromaticus/' which is now recognised 
as one of the Andropogon family. Acorns calciums grows best by 
the banl'is of rivers and in marshy ground, being plentiful by the 
rivers in Norfolk. It is now cultivated in damp marshy places in 
India and Burmah. In warm climates it develops greater fragrance 
than it does in England. From the lower part of the thick, jointed 
rliizome the plants send down numerous long, slender roots, but 
it is from the rhizome itself that the essential oil is distilled. 

The dried rhizome is found in commerce as flattened pieces 
from 4 to G inches long and about -jj inch thick. It is of a yellowish 
brovai or favm colour externally. In India the rhizome is used in 
the preparation of an aromatic vinegar. In Europe the rhizome is 
used in the form of powder as a constituent of toilet and sachet 
powders, but its use has decreased of late years. 

According to Russell (Jonr. Amer. Clicm. Soc., 1915, 37, 2387), 
aU parts of the plant contain an essential oil, which varies in 
characters with the portion of the plant from which it is 

The normal essential oil of sweet flag, which is used to some 
extent as a perfume material, and also as an ingredient in the 
flavour of gin and some types of beer, is distilled from the 
rhizomes. Its specific gravity varies from 0-950 to 0-970 ; optical 
rotation, 9° to -- 35'" ; refractive index, 1-5000 to 1-5080 ; and 
ester value from 5 to 20. 

It contains pincnc. camphenc, camphor, a sesquiterpene termed 
calamcnc, a sesquiterpene alcohol, eiigcnol, hcptylic acid, palmitic 
acid, and asarvlic aldehvde. 

There is a Japanese calamus oil, distilled from Calavuis sgjuxius. 
which diflers somewhat from the oil from C. aromaiicus, but 
resembles it in general characters. 

AFRICAN COPAIBA OIL. — Sec “ Hardwickia Balsams." 

AGLAIA FLOWERS. — ^The flowers of AgJaici odoraia, 
known locally as Lan-hva or Yn-chv-Ian, arc used by the Chinese 
for the purpose of scenting tea. 

AJOWAN SEED OIL. — Ajowan seed is the fruit of Ptychotis 
Ajoivaii {Carinn Ajouxai, Garum cojMcwn), u plant known as 

true bishop’s^ weed. ' The plant is cultivated in many parts 
of Egjpt, Persia, Afghanistan, and Bengal. It is indigenous to 
India. The seed yields from 3 to 4 per cent, of essential oil, 
having a powej-ful odour of thymol. In addition to its principal 



constituent, .tliymol, the oil contains cymene, pinene, dipentene, 
and terpinene. The oil is used on a large scale for the preparation 
of thymol {q.v.). In the native bazaars of India the oil is allowed 
to evaporate^ spontaneously, and the crude thymol is sold under 
the name Ajivain-ha~pliul (Flowers of Ajowan). The odour of 
the oil is pungently aromatic. The plant is known by the following 
vernacular names in the East : — 

Arabic . 
Persian . 
Duldini . 
Telegu . 
Bengali ' . 


Nanhhah and Zinyan. 



Omamu or Vamamu. 
Ayamodaham and Eomam. 

Ajvain or Ajvan. 
Vova-sada and Vova. 


Experimental cultivations have been started in the West Indies, 
but so far they have not 3 delded commercially successful results. 

The essential oil has a specific gravity 0*910 to 0*930 ; optical 
rotation, -{-.1° to + 5° ; and refractive index, 1*4980 to 1*5005. 
It contains from 45 to 60 per cent, of thymol, and serves as a raw 
material for the extraction of this important bod 3 ^ 

Bodh Baj Sobti and Puran Singh (P. ds E. 0. R., 1923, 399) 
state that in the thymol manufactory of the Scindia Chemical 
Laboratories, Gwalior, they found a large fraction of a dark 
residual oil which would not crystallise at aU— left as it was after 
the whole of the thymol was crystallised out from the phenol 
fraction of the ajowan oil wliich was obtained by shaldng the oil 
with caustic soda solution. It seemed interesting to identify 
this material, especially when the presence of carvacrol in ajowan 
oil had yet to be confirmed. {Vide Parrjr, “The Chemistry of 
Essential Oils,” 3rd edition, vol. i., p. 303.) 

Large quantities of this fraction of the phenols were available 
in the thymol refinery. After repeated distillation and refrigera- 
tion, these gave sufficient quantities of a non-crystallising phenol 
distilling over between 236° and 240° C. at 746 mm. pressure. It 
had the following physical constants : — 

Specific gravity at 29*0° C. ’ . 0*9712 

Optical rotation . . .0 

Refractive index at 28° . . 1*5230 

7 " 


r c 

Oil combustion found | 

{ c 

Theoretical CioHi.jO | 

SOTO per cent. 

Tliere are a good number of phenols of the formula OiqHi.iO 
n'hieh have their boiling points near 235° 0. In order to eliminate 
some of these, tlie methyl ether was prepared. 

There are four possible isomeric methyl ethers which have their 
boiling points near 21G° C., viz. 

(1) Meth}-! ether of 4-oxy-3-in-opyl-l-methyl benzene, boiling 

point 210° to 218° C. 

(2) IMothyl ether of O-oxy-S-isopropjd-l-meth^d benzene, boiling 

point 217° C. 

(3) Method ether of 2-ox3'-4-isopropyl- 1-methyl benzene (carva- 

croi), boiling point 216-8° C. 

(4) Methyl ether" of 3-oxy-4-isopropyl-l-mcthyl benzene (thy- 

mol), boiling pomt 210-20° C. 

Fm-ther. the metiiyl ether, on oxidation with 5 per cent, 
potassium permanganate in alkaline solution, gives an oxymethyl- 
dicarboxylic acid hamng a definite melting point. It was prepared 
as follows : — 

The methyl ether was suspended m strong sodium carbonate 
solution and kept ice cold. Five per cent, potassium permanganate 
solution (the calculated quantity) was added in portions until the 
coloui’ was slightly permanent. To destroj’’ this, a little alcohol 
was added. Manganese dioxide was filtered off and washed with 
hot water. The filtrate was taken donm to a small volume on a 
water bath, and then acidified with hydrochloric acid. The 
methoxy acid thus obtained was recrystallised from • alcohol. 
Its melting point was 277° C. 

J^Iethyl ether of 4-oxy-3-prop3d-l-methyl benzene and 6-oxy-3-iso- 
propjd-l-metlijd benzene give the same oxy-meth3d-dicarboxylic 
acid melting point 201° C ; while ineth3d ethers of 2-oxy-4-iso- 
prop3d-l-meth3d benzene (car vacrol and 3-oxy-4-isoprop3d-l-meth3d 
benzene (th3-mol) give the same ox3nneth3’'-dicarbox3dic acid which 
melts at 277° C. Therefore, the phenol under investigation can be 
either th3miol or carvacrol. 

A drop of ferric chloride was added to an alkaline solution of 
this phenol ; it was coloured green, and after some time changed 
to a dark brown colour. This led the authors to ‘suspect the 
presence of carvacrol. This was further confirmed b3'' the colour 
produced b3' heating it vith formaldeltydc (Hermann Bndermann, 



Jour. Soc. Ghem. Ind., 1896, 791-792). A little of tlie substance 
Avas dissolred in commercial formalin, the solution evaporated 
nearl}’’ to dryness at a low temperature, and concentrated sulphuric 
acid added. The solid residue was coloured orange. To be sure 
of the colom’ reactions, a little pure thymol and carvacrol were 
treated under similar conditions. Tlie colour produced by the 
caiwacrol sample was exactly similar to that produced by the 
fraction under investigation. For furtlier confirmation, the nitroso 
compmmd was prepared, the melting point of wliich was 153° C. 

ALCOHOL. — ^Alcohol is the most important substance used 
by- the perfumer. So many^ of the substances used in perfumery 
are only soluble in organic solvents, that water is of comparatively’' 
little use. The solvent for the perfumer must be very volatile, 
and must be sufficiently free from odour not to interfere with the 
perfume value of the ingredients dissolved therein. - Prolonged 
experience has demonstrated the fact that alcohol is the best 
solvent which meets the general requhements of the perfumer. 
There are other solvents, such as isopropyd alcohol (q.v.), which 
are of considerable use, but there is no other that will effectively^ 
replace ordinary alcohol without so7nc disadvantage. 

Alcohol, or ethyl alcohol, is a substance which is obtained 
universally by fermentation processes. It results from the 
decomposition of sugar by means of the y-east organism, which 
breaks sugar dovm into alcohol and various other secondary’ 
constituents. For the perfumer it is of the highest importance 
that the alcohol employed should be as free as possible from such 
secondary constituents, and have as little odour as possible. In 
this country’ the alcohol generally’ preferred is grain spirit, Avliich 
is as free from secondary’ constituents as possible. 

Pure or absolute alcohol, that is, alcohol of 100 per cent, 
strength, C 2 H 5 OH, is a colourless volatile liquid of faint, delicate 
odom’, having a specific gravity 0-794 at 15-5°, and boiling at 7S° 
to 79°. 

The perfumer rarely’ uses alcohol of this strength, as, of course, 
the duty on alcohol in this country is exceedingly high. His aim 
is, therefore, to use the lowest strength alcohol possible com- 
patible ■with efficiency in his products. That efficiency demands 
that the necessary ingredients shall be perfectly soluble, and that 
the finished product shall be sufficiently volatile. The considera- 
tions that arise, then, are : firstly, the determination of the 
strength of the alcohol to be used ; secondly, the tests necessary 
to detect impurities in the alcohol ; and thirdly, as is veiy fre- 


quently necessary, the estimation of tiie alcohol in the finished 

(1) For all practical purposes the perfumer can rely on the 
specific gravity of the alcohol as a correct measure of its strength. 
This is true if it he mi.vod with nothing else but water ; otherwise 
it is not true, and the innscnce of foreign substances must be 
allowed for. 

A term frequently used is proof spirit, together with the 
expression “ degrees under or over proof.” The term iwoof 
spirit had its origin einpii’ically. The excise ofiiccrs in early days 
tested alcohol for duty purposes by pouring a given amount on 
a given weight of gun])owder. If it Avas below a certain strength, 
the gunpowder did not ignite on the application of a light ; if 
above a certain (empirical) strength, it did ignite. Hence the 
terms under or over proof. To-day, proof spirit is legally defined 
as alcohol of such a strength that, at 51°, 13 volumes shall weigh 
as much as 12 volumes of Avatcr. 

Proof spirit has a specific gi’aAuty at 15-5° C., 0-910S, and 
contains 45'-2S per cent, of alcohol by AA-cight, or 57-] per cent, by 
A'olumc. The expressions Ainder or oA'er joroof mean as follows. 
Ii a samjfie of alcohol contains as inuch alcohol as corresponds 
AA-ith SO per cent, of proof strength, it is 20° vndcr proof. If it 
eontains alcohol corresponding AA'itli ] 20 per cent, of proof strength, 
it is 20° o?-c?' proof. The folloAA'ing table gives the strength of 
mixtures of aleohol and Avatcr by volume. Tlieso figures arc from 
the table in use in the GoA-ernment labor.atoiy : — 

cravitv , 



.Vlt'Oim. ; 






III GO r. 

(i:r,v C.) 




v/elpht. ! 





999 1 






1-07 1 

i 2-33 


2 02 


1 3-52 

99G ' 

‘ 2-71 

2-17 I 




2’73 1 

1 0-98 

991 ' 


3-31 ! 

' 7-2-1 

993 i 




992 ! 



i 9-82 

991 ' 




990 1 

7-] 8 



989 1 




988 ' 


8-80 ’ 

: 7-08 


nt 00' 1 \ 
(Lfr.V C.) 










\vcipht . 






















i 14-13 










! 27-99 























nt 00'' r, 
(15*5® C.) 

j Altsoluto Alcohol. 









































































958 ' 






























! 33-81 i 




34-37 i 





/ 3 -OiJ 














































48-57 i 




































at CO’ i'. 

(15-5° C.) 




















5 - 1-14 







924 . 

















































60-19 • 




















; 62-39 




: 62-83 





























































































Specific 1 

Absolute AlcolioL 






at 00"' P. 
(15-5= C.) 

Absolute Alcohol. 





nt ro^ r. 
{15‘5= C,) 

volume, ] 







884 i 


72-34 ; 







883 , 

72-74 1 







73-13 , 








73-52 ' 









73-91 * 







879 > 

74-30 • 
















75-06 ! 








75-44 1 







875 ' 

75-82 1 





874 , 

76-19 1 






873 ■ 

76-57 ; 







872 ' 

76-94 : 







77*32 1 



S 2 d 






























79-17 ' 






865 ' 



















817 ! 

9 - 1-71 





141 - 28 - 

1 816 





80-97 1 


1 - 11-91 

' 815 




860 ! 

81-32 1 






859 1 

81-68 ! 







858 1 

82-03 ; 






857 1 

82-38 ! 

! 76-30 






856 : 

82-73 ’ 

' 76-71 





855 ' 


j 77-12 






! 77-53 





853 ' 


' 77-94 






852 i 


I 78-35 





851 i 


' 78-76 






850 1 


i 79-17 





849 1 


1 79-58 






848 ’ 


i 79-98 






847 . 


' 80-39 














845 ■ 















843 ; 







842 i 






99-22 - 


841 ! 





















' 100-00 





(2) Detection of Impurities . — ^The impurities in alcohol will 
depend to a large extent on the source of the saccharine solution 
by the fermentation of which the alcohol is obtained. In England, 
grain starch is the principal soiirce of alcohol ; in France it is 
vciy largely beet sugar ; in Germany, potato starch ; and in the 
United States maize is emplo5’'ed to a very large extent. Rice 
flour is used considerably in Eastern countries. Grain spirit and 
beet sugar sphit are usually most valued, as they contain less of 
the objectionable impurities which tend to spoil the odour of 

The principal impurities to bo guarded against, apart from delibe- 
I'ate additions such as appreciable quantities of methyl or isopropyl 
alcohols, arc aldehydes, esters, and the higher alcohols. These 
bodies, associated in different proportions in alcohols having 
different origins, are general^ described under the name fusel oil. 
These impurities are largely removed by diluting the alcohol with 
water, when a certain amount of the impurities are thrown out of 
solution, and may be separated, the alcohol being then again 
concentrated by fractional distillation, the first runnings and the 
tailmgs being rejected for retreatment, the middle runnings being 
almost pure alcohol, mixed with a little water. For very special 
purposes, alcohol (rectified spiiit, sphit of wine) may be still 
further pmified by treatment with chemicals such as silver 
nitrate, to decompose the last traces of aldehyde, and again 
distilling. Such highly purified alcohol is often Icnowm as Cologne 
sphit, and is suitable for use in the most delicate perfumes. 

The following test, originally due to MuUilven and Scudder, will 
detect as little as 2 per cent, of methyl alcohol in ethyl alcohol. 
One cubic centimetre of the sample is diluted to 10 c.c. with 
water, or, if already dilute, to about 10 per cent, strength. A 
copiDcr wire sphal is made by winding 1 metre of copper wire, 
about No. 18 gauge, round a glass rod 7 mm. thick, making a 
coil 30 mm. long, the remaining portion of the wire being used as 
a handle. The coil is heated to redness in a bunsen flame, and at 
once immersed in the liquid contained in a test-tube. This is 
repeated five or six times, the- tube being kept in cold water in 
order to prevent the temperature rising too much. . The liquid is 
filtered into a wide test-tube and boiled very gently. If an odour 
of acetaldehyde is perceived, the boiling is continued until it has 
disappeared. The liquid is now cooled, and a drop of a O' 6 per 
cent, solution of resorcin is added. A portion of the liquid is then ' 
carefully floated on to strong sulphmic acid, allowed to stand, and 



then gently rotated. If a rose red-ring ap23ears at the contact zone, 
methyl alcohol is not present to the extent of more than 2 per 
cent. — a most unlikely quantity for anj”" deliberate adulteration. 

Having determined the strength of the alcohol and the absence 
of methjd alcohol, the following determinations are, if deemed 
necessary, made ; — 

(а) Total Solid Bcsiclue . — If 50 c.c. be evaporated on a water 
bath, the solid residue should be so slight as to be unweighable. 

(б) Free Acids . — If a few drops of phenoljDhthalcin be added to 
•50 c.c. of the alcohol, 0-2 c.c. of decinorraal barj^ta solution should 
cause a jhnlc colour to develop. A good i^erfume spuit should 
contain less than 3 parts j^er 100,000 (calculated as absolute 
alcohol) of free acids calculated as acetic acid. 

(c) Total Aldehydes . — The best j)rocess for the determination of 
the aldeh 3 'des is the official 2 )rocess of the French Government. 
This is carried out as follows. A standard solution of 0-1 gram 
of aldeh 3 ’de per litre Is made b 3 ’’ dissolving 1*386 grams of aldeh 3 ’de 
ammonia crystals (= 1 gram of aldeln'de) in about 50 c.c. of jjure 
95 per cent, alcohol. 22*7 c.c. of normal sulphuric acid solution 
are added, when ammonium sulphate is precipitated. The liquid 
is made up to 100 c.c. vith 95 per cent, alcohol, and another 0*8 c.c. 
is added to compensate for the precipitated ammonium sulphate. 
The liquid is left for twelve hours, after being ■well shaken, and 
filtered. About 90 c.c. of water are added, and the whole diluted 
to 1 litre with 50 i^er cent, alcohol. This is now practicall 3 ’’ a 
50 per cent, alcoholic solution, and when diluted ten times with 
50 per cent, alcohol, is a solution containing 0*1 gram of aldeltyde 
]ocr litre, or 1 in 10,000. 

A fuch sine-sulphurous acid solution is prej^ared b 3 ’ mixing 30 c.c. 
of a 0*1 per cent, solution of fuchsine in 95 per cent, alcohol, 
15 c.c. of a solution of sodium bisulphite in water (specific gravity 
= 1-30S), and 30 c.c. of water. The mixtiu’c is shaken and 
allowed to stand for an hour. Fifteen cubic centimetres of 
30 per cent, sulphuric acid are then added, and the liquid made 
up to 250 c.c. vith 50 per cent, alcohol. 

The sample to be tested is diluted vith water to 50 per cent, 
strength and 10 c.c. of the standard solution is treated Avith 4 c.c., 
of the fuchsine -sulphurous acid solution, and the colour developed 
is matched by adding 4 c.c. of the fuchsme-sulphurous acid solution 
to sufficient of the diluted sample. From the amount used the 
quantity of aldeh 3 ’-des is calculated, and should be returned in 
parts per 100,000 of absolute alcohol. Ver}’’ fine samples contain 



less than 1 part, and should not contain more than about 2-5 to 
3‘5 parts per 100,000 of absolute alcohol. 

{d) Esters . — The aldehydes are first removed by boiling for an 
hour -with 3 per cent; of metaphenylene diamine under a reflux 
condenser. The liquid is then distfiled, 90 per cent, being collected, 
and the distfilate made up to its original volume. The esters are 
now determined by saponification in the usual manner, and are 
returned as parts of ethyl acetate per 100,000 of absolute alcohol. 
Crude grain spirit may contain 20 to 50 parts per 100,000, but the 
finest samples will contain only 4 to 10 parts. 

(e) Higher Alcohols . — ^There is no exact method of carryuig out 
this determination, but Marquardt’s process, modified by Allen 
and Schridowitz {Jour. 8oc. Chem. Ind., 1902, 815), probably gives 
the best results obtainable. Two hundred cubic centimetres of 
the alcohol are boiled under a reflux condenser with 0-2 gram of 
KOH for one hour, and the liquid distfiled until 180 c.c. have 
passed over. Steam is passed through the' residue until 300 c.c. 
are collected. The alcoholic strength should be as near 50 per cent, 
as possible, either by the addition of pure alcohol or water, iE and 
as necessary. The exact vqlume is noted, and 100 c.c. taken for 
the distillation. This is mixed with saturated brine until the 
specific gravit}’- is 1-100. The liquid is then extracted with three 
successive quantities of carbon tetrachloride of extreme purity, 
the separated carbon tetraclfioride shaken with a 50 per cent, 
solution of potassium sulphate, and finally separated and filtered. 
It is then oxidised by a solution of 5 gr. of potassium biclmomate, 
2 gr. of sulphuric acid, and 10 c.c. of water on a water bath 
for eight hours, under an ejEficient condenser. The liquid is 
distfiled, firstly over a bunsen burner, and then with steam, until 
about 300 c.c. have been collected. The carbon tetrachloride is 
separated and washed with^water, the washings being added to 
the aqueous distillate. This is then titrated with decinormal 
baryta, using phenolphthalein as indicator, after traces of mineral 
acid have first been neutralised to methyl orange. It is usual to 
return the higher alcohols calculated as amyl alcohol, so that the 
acids so found are calculated to valerianic acid. Each cubic 
centimetre of decinormal allrali is equivalent to 0-0088 gram of 
amyl alcohol (or 0-0074 gram of butyl alcohol). Calculated to 
100,000 parts of absolute alcohol, the best perfumery spuit should 
contain less than 10 parts, sometimes as low as 3 parts, per 

Finally, it is often necessary to determine the strength of mixed 



perfumes in alcohol when the specific gravity is useless, owing to 
the presence of essential oils, etc. The following process (Thorpe 
and Holmes, Jour. Cliem. Soc., l'903, 83, 314) may he used. 
Care should he taken that all measurements, etc., are made at 
exactly 15-.5°. Twenty-five cubic centimetres of the sample are 
mixed with about 125 c.c. of water, and the whole saturated with 
salt in a separator. The mixture is extracted twice with from 
50 to 80 c.c. of petroleum ether, the mixed petroleum extracts 
washed tvice •with brine, and the washings added to the original 
liquid. The Hquid is distilled until all the alcohol has passed over, 
and the distillate diluted to 100 c.c. and its specific gravity taken. 
From this the amount of alcohol is found, and multiplied by 4 
gives the percentage in the original sample. 

(For further details, see E. J. Parry, “ Food an^ Drugs,” vol. i., 
Scott, Greenwood & Co,, London.) 

ALCOHOLS. — ^The group of bodies kno'Rm under the generic 
name ” alcohols ” play a very important part in the art of 
perfumery, both from the natural and the synthetic points of 
■^dew. The alcohols may, for general purposes, be described as 
bodies contaming one or more hydroxyl (OH) groups, which are 
characterised bj’’ then’ ability by reactions "with acids to exchange 
themselves for acid residues, and so give rise to esters correspond- 
ing with salts of mineral acids. Thej’- are distinguished from the 
phenols — bodies belonging entirely to the closed-chain group of 
compounds — where one or more of the hydrogen atoms of the 
ring have been substituted by OH groupsr The phenols are 
sharpty differentiated from the alcohols by their acid nature, on 
account of "s^hich they readily combine •Rntli aUcalis to form alkaline 

Alcohols are termed monohj^dric, dihydric, etc., according to 
the number of hydi'oxyl groups they contain. Thus ordmary 
“ alcohol,” or, more properly, ethyl alcohol CgHg.OH, is a" 
monohydric alcohol ; ethjdene gtycol CoH4(OH)2 is a dili5rfric 
alcohol ; glycerine C3H5(OH)3 is a triliydiic alcohol, etc., etc. 
The monohydric alcohols are the most important of those which 
are found naturally in perfume materials, and of those which are 
manufactured artificially. They are sub-divided into three well- 
marked groups ; these are the primary, secondary, and tertiary 

The primal}^ alcohols are characterised by the hydrogen being 
linked by. bivalent oxygen to a univalent radical. Thus geraniol, 
(CioHj^^)' — 0 — ^H has the univalent radical (G10H17)' linlced to 



the hydrogen atom of the hydroxyl group by the bivalent atom 
of oxj^gen. The primary alcohols are characterised by being 
oxidised (generally) with the formation of aldehydes containing 
the COH group, “and thence to acids containing the CO OH group. 
In primary alcohols, therefore, the OH group is attached to a 
— CHg — group. 

In secondary alcohols the OH group is attached to a bivalent 

/T? f 

radical thus, H.O — 0E[\^ , "sphere R and represent other 

radicals attached to the linking carbon atom. Thus isopropyl 

alcohol, wliich may be represented by the formula OH, 

is a secondary alcohol. They are characterised by not yielding 
aldehydes on oxidation, but ketones containing the — CO — group. 
Finally, where the hydrogen is linlced up to a trivalent radicle, 

thus, H — 0 — C;^R' , the alcohol is termed tertiary. These 

alcohols 3 deld neither aldehydes nor ketones on oxidation, but are 


decomposed by the process. Trimethyl carbinol H.O.C^CHg is 


an example of a tertiary alcohol. 

The principal alcohols found naturally in essential oils, or manu- 
factured artificially for perfumery purposes, are monohydric and 
primary. They exist to a considerable extent in the free state, 
such as geraniol in palmarosa oil, and also in the form of esters, 
such as geraniol as geranyl tiglate in geranium oil, and linalol as 
Knalyl acetate in bergamot and lavender oils. The more im- 
portant of these will be found described under their particular 
name, and methods for their determination will be found under 
the headings'” Alcohols, Determination of,” and “ Esters.” 

The alcohols soluble in water are not, except possibly in minute 
ti’aces, to be found in distilled essential oils, as they have, of course, 
if present, been dissolved 'out in the distillation waters. The 
alcohols present in essential oils are either the open-chain alcohols, 
such as the alcohols usually classed as " fatty alcohols ” and those 
sometimes classified, as a matter of convenience, as the open-chain 
“ terpene ” alcohols of which geraniol is the type ; or they are 
the closed-chain alcohols of the typical “ aromatic ” or ” cyclic ” 
series such as benzyl alcohol, or of the closed-chain ” terpene ” 
series such as menthol. 




Belial {Compies Bendv.s, 1919, 168, 945 ; and Boure-Bertrand 
Fils, Bulletin, April, 1920, 117), lias dealt witli the isolation of 
alcohols in a pure condition after ph^’^sical methods, such as 
fractional distillation, have acliiered all that is possible. He refers 
to Pasteur’s vrork on the separation of the two alcohols, contained 
in the amyl alcohol of fermentation, by means of convertuig them 
into sulphuric ethers, acids, and barium salts of different solubffity. 
Later, as he points out, the results of the researches of A. Haller 
{Coinpies Beudus, 1889, 108, 140 ; 1890, 110, 580) on the borncols 
were more general in their scope. They relate to the properties 
of dibasic organic acids of acting on alcohols to give acid ethereal 
salts soluble m alkalies, and whose solutions when saponified 
liberate the original alcohols. The application of this method to 
terpene alcohols has been the subject of criticisms by Tiemann and 
Eh’iiger {Berichte, 1896, 29, 901). Dodge, in his investigations 
of oil of citronella, and numerous other chemists have, however, 
utihsed tins method. HaUer has a Iso recommended it for obtaining 
pure methyl alcohol bj* preparing the acid phthalate of methjd 
bj^ means of phthahc anhydride. 

Bouveault has proposed the use of pyruvic acid to identify the 
alcohols and separate them from a mixtm’e. He converted the 
esters to which they gave rise into semi-carbazones, whence the 
alcohols can be regenerated by saponification. 

Phenyl isocyanate and diphenyl-carbamyl chloride have since 
been used to obtain urethanes. 

A. Behai has taken up an old investigation by Liebig and 
Wohler, and perfected a method that leads to the formation of 
allophai ates together withm'ethanes. It consists in causing cyanic 
acid to react on alcohols. The urethanes, however, are generally 
only bj- -products of the reaction. 

■This method has been apphed to the primary, secondar 3 ^ and 
tertiarj' alcohols, wLereas none of the preceding methods were 
available for the last named. The author has lilcevise obtained 
good results mth terpene alcohols, those of the benzene series, 
and lastty with the phenols. 

The method emploj^ed for the preparation of these derivatives 
is as follows : — 

A current of c^-anic acid gas is passed into the cooled alcohol. 
The gas is prepared by' the depclj^'merisation of cyanuric acid. 
The latter is obtained by’ Behai by causing chlorine to act on urea, 
then precipitating the cyanuric acid with ammonia cal copper 
sulphate and decomposing the double salt of copper thus formed. 



bj' nitric acid. The cyannric acid is placed in a tube of 12 mm. 
internal diameter, wliich is heated to a dark red from front to 
back. A current of carbonic acid gas is passed sloudj’- through the 
tube, in front of which is arranged a chamber 30 cm. long. The 
tube leading the cyanic acid gas into the alcohol has a -wide mouth. 
The alcohol rapidly becomes heated, and then suddenly swells up 
as a mass of crystals is formed. The crystals, after being cooled, 
are pounded in a mortar with absolute ether. The whole is their 
filtered and washed udth ether until the ether filtrate no longer 
leaves a residue on evaporation. The ether thus removes the 
uncombmed alcohol and the urethane, which is always formed to 
a greater or less extent. 

The insoluble I’esidue consists of the allophanate impregnated 
v-ith cyanuric acid. The aUophanate is then dried until the cyanic 
odour disappears. It is then dissolved in warm absolute alcohol, 
benzene or acetone, from which it cr3fstallises on cooling. The 
product is generally pure with the first crystallisation, and°further 
crystallisations are needless. 

In the case of solid alcohols, the author operates with an ethereal 
solution. All the allophanates thus obtained are crystalline, 
colourless, and inodorous substances. Thej^ are very slightl}^ 
soluble in cold ether and are somewhat more soluble in cold 
alcohol, though then' solubility is still very slight. 

• In the acyclic series the tertiary allophanates are easily 
pponified by boiling water. The alcohol is regenerated and urea 
is formed with liberation of carbonic acid. 

The primary and secondary allophanates are saponified with 
gieater difiicultj’’, and in most cases require a boiling aqueous 
solution of caustic allcali. 

By operating on 5 gi-ams of the alcohol or on a quantity of sub- 
stance containing 5 grams, the alcohol may be easily isolated and 
identified by the nielting point of its allophanate, the alcohol then 
being regenerated in order to determine its physical constants. 

Among the terpene alcohols, linalol behaves abnormally, and 
Behai suggests that it is not an alcohol, but an oxide. 

The cyclic alcohols, with the exception of terpineol, follow the 
normal rule. 

^ In the arylalkyl series the author has observed some marked 
discrepancies in substances containing phenol functions. But if 
the phenol function is esterified, the reaction becomes normal. 
In the case of phenol compounds in presence of alcohols, it is easj’- 
to eliminate the former by treatment vdth alkali. 



P E R F U 21 KEY 

ilic alcoliols with an ctlij*lene hydrocarbon function also give 
normal alJophanatcs. 

Hofmann {ISerjclRc, 1871. 4, 2GS) was the first to give a theory 
of the formation of tlie allophanates, and attributed it to the 
])rc^ious formation of a urethane, on whieh the cyanic acid 
sulxserpicntly acted. Behai is inclined to think that dieyanic acid 
ib formed, and that thi.s at the moment of its foi’ination reacts on 
the alcohol present. Before the treatment with cyanic acid, he 
advise.-^ a fractional distillation, which should be carried as far as 
])ossiblc, after preliminary tj-catments with caustic soda and 

The following are the melting points of the alloifiianates of the 
imdermentioncd alcohols : — 


Molt in e: 




Elhyi . 

Xormal butyl 

Hexyl . 

Octyl . 

Xonyl . 

Hecyl . 


Allyl . 





i 190° 


Amyl .... 

; 152° 

119-5° to 


' 121° 




1 80-5° 








Secondary phonvletlivl. 



100° : 

Cyclolicxylbutanyl ' . 


157° , 

Ginnamyi . 


158° i 


• 179-5° 




155-5° to 

; i\Icnl]iyl 

• 213° 

150° 1 


; 192-5° 

159-5° I 

Tertiary mcnlliyl 

i 187° 

105° , 

, Isopiilegyl . . 

! 219° 

159-5° j 


1 180° 


Most^ alcohols form numerous wcll-characteriscd ciystalline 
derivatives, which are useful both for identification juirposcs and 
for purifying the alcohols. 

Amongst these may be mentioned the acid esters of phthalic 
acid. (See Comjiics Pewhis, 1SS9, 108. 130S ; 1S96, 1S2 SGo • 
Bull Eoc. Chim., 1900, 23, 5-12; Pharm. Zeil., 1899, 44, 258- 
Bcnchic, 1910, 43, 1893.) The general method of the formation 
of these bodies is as follows : — 

Fifty grams of the oil (saponified if necessary) containing the . 
free alcoliol (or a fraction of the oil rich in the free alcohol) arc 


P E R F U M K R )■ 

mixed with 50 grams of freshly prepared phthalic anhydride and 
25 gi’ams of absolutely dry benzene. The mixture is heated to 
110° to 120° for ten hours in a flask under a reflux condenser. 
The mixture is cooled, an equal volume of water added, and 
caustic soda solution added until the mass is just alkaline to 
phenolphthalein. The mixture is extracted several times vith 
ether to remove oil not acted upon, and the filtered alkaline liquid 
is acidified vitli concentrated hydrochloric acid. The oily phthalate 
.‘separates, is washed with water, and dried. To recover the 
.alcohols from the acid phthalatcs, the latter are saponified vdth 
alcoholic potash, the precipitated potassium phthalate filtered off, 
the ethyl alcohol evaporated off, and the rc.sidual insoluble alcohols 
arc washed and dried. 

The phenjd-urethanes resulting from the reaction of phenyl 
isocyanate and the alcohol are also most useful cry.stallinc com- 
pounds for identifying the alcohols, as are also the naphthjd- 
urethanes. In the preparation of these bodies works on organic 
chemistry should be consulted. 

For a suggested method of separating primary, secondary, and 
tertiary alcohols, see E. Ernrnett Reid, Jow. Amer. Cliom. Soc., 
1917, 1249. 

M. D. 

OILS. — ^The principles on which such determinations are made 
are based on the conversion of the free alcohoLs irrto acetates by 
the action of acetic anhydride and the estimation of the esters 
formed. When the oil contains both ester-s and free alcohols, the 
calculation becomes somewhat complicated, since the alcohols 
increase in weight on acetylatiorr, whilst the natrrral esters are 
unaffected. It should be pointed' out that, as in the process of 
determining the percentage of esters, the results are not strictfy 
accm'ate chemical determinations, but are based on the assumption 
that the predominating alcohol is the only substance reactirrg with 
acetic anlr 3 ’^dride. 

The details of the method generally adopted, which should be 
strictly adhered to, are as follows : — 

Ten cubic centimetres of the oil are gently boiled vdth 20 c.c. 
acetic anhj'^dride and 2 grams of fused anhydrous sodium acetate, 
in a 100 c:c. round-bottomed flask fitted vith a reflux condenser, 
for two hours. The contents of the flask are allowed to cool, 
100 c.c. of water added, and the mixture gently warmed on a water 
bath to decompose the excess of acetic anhydride. The mixtine 


P JC R F i: 21 E PY 

ip then transferred to a sci}arator. the aqueous la^'or rejected, and 
tJie oil washed with successive quantities of 50 c.c. each of brine 
solution containing 1 per cent, of caustic soda and a little idienol- 
phthalein until the washings are free from acidity. The oil is then 
dried hiy stirring with a little anhydrous sulphate of soda, and 
filtered bright through paper. 

A suitable quantity of the oil (2 to 6 grains, according to the 
proportion of esters present) is weighed out and saponified with 
40 c.e.-of semi-normal alcoholic potash solution as described under 
the determination of esters. The percentage of total alcohols in 
the original oil is then calculated from the following formula : — 


10(W - 0-042N) 

where x is the percentage of total alcohols in the original oil, 

X is the number of cubic centimetres of normal alkali used, 
W is the weight of acctylated oil taken. 

To obtain the percentage of free alcohols, the saponification value 
of the original oil must be determined, the saponification value of 
the acetylated oil calculated, and the following formula will then 

^ r r 1 1 1 (^ — Y]y 

Percentage of free alcohols = — rr 

° 0-42010(1335-5 — h) 

where a = saponification value of the original oil, 

b — ,, acetylated oil, 

y = molecular weight of the alcohol (monatomic). 

In some cases, notably linalol and terpineol, the alcoliol is 
partially decomposed b}’’ acetylation in the above described 
manner. Boulez {Bvll. Soc. Chim., iv., 1907, i., 117) has recom- 
mended diluting 5 grams of oils containing these alcohols with 
25 gi’ams of purified tiu’pentine and boiling the mixture with 
40 c.c. of acetic anhydride and 3 to 4 grams of anh3!'drous sodium 
acetate. A “ blank " experiment to allow for the apparent alcohol 
value of the turpentine must, of course, be carried out. (See also 
SchimmeVs Re])ori, April, 1907.) 

Glicliitch {Bull. Soc. GMm., iv., 1923, 33, 1284, and P. cC: 
E. 0. JR., 1923, 401) has proposed a method depending on the use 
of a mixtiue of absolute formic acid and acetic anlij^'dride. This 
method is based upon Beliaks discovery, in 1900, that the mixed 
anhjulride of formic and acetic acids reacts in the cold with 
alcohols to give formates exclusively, while phenols remain 
unchanged. Behai obtained complex results with linalol oiving 


P E P P U M E P 

to the fact that he worked at 50° and used an insufficiently low 
vacuum for the distillation of the product. It is now shown that 
esterification of linalol is complete in seventy-two hours at 20° to 
25°, the conversion into geranyl and terpinyl formates being 
neghgibly small. The presence of acetic acid, acetic anliydride, 
and formic acid in the'acetoformic anhydride does not affect the 
results, as these compounds form no addition products vdth 
terpenes and sesquiterpenes in the absence of mineral acid. 

Preparation of Acetoformic Anhydride. — One part of absolute 
formic acid (D 1-22/15°) is added slowlj’’ with constant agitation 
to 2 parts of chlorine-free acetic anh^’^ffiL'ide (100 per cent.), the 
temperature being kept below 15°. The mLvture is heated during 
fifteen minutes to 50° and rapidly cooled. It is kept in a bottle 
TOth an emery stopper. 

Method of Estimation. — ^Ten cubic centimetres of the alcohol to 
be estimated are added to 15 c.c. of acetoformic anliydride in a 
30 c.c. flask closed ufith an emery stopper. The mixture is well 
shaken, plunged into a bath of ice water (which need not be 
renewed), and allowed to remain for seventy-two to ninety-six 
hours. It is often possible to esterify in seventy-two hours at 
20° to 25°. A greater excess of acetoformic anhydride or a longer 
time than ninety-six hours has no effect, good or bad. A smaUer 
quantity of the reagent is insufficient for pure linalol. The whole 
is then poured into 50 c.c. of cold water, well agitated, and left for 
two hom’s without heating. It is then washed successively with 
50 c.c. of w’^ater, 50 c.c. of 5 per cent. NaHCOs solution, and 
finally twice with 50 c.c. of w^ater. The esterified oil is dried and 
saponified as usual, one and a half hours’ hydrolysis bemg given 
to ensure the complete saponification of traces of terpinyl 

The alcohol content of the original oil is calculated from the 
formula — 

n' X M 

lQ.{p.n' X 0-028) 

where n' — cubic centimetres normal KOH used up, 
p — grams of oil taken, 

M = molecular w^eight of the alcohol. 

Pure Imalol prepared by repeated fractionation of rosewood 
oil was used as a test sample. It was soluble in 14 volumes of 
50 per cent, alcohol, and had boiling point 63° to 63-5°/2 mm. or 
82-3° to 82-6°/ 10 mm., D 0-8630/21°, n 1-4605, and optical rota- 


P KB F (■ M FRY 

tioii — 17' 30°. The percentage of linalol determined by the above 
method was ; — 

24 hours’ formylation 

Per cent. 


48 „ 



,, 3 , 


00 „ 


144 ., 




It has been proposed to determuie citronellol in the presence of 
geraniol by means of form 3 ’]ation, instead of by acetjdation, on 
the supposition tiiat heating Tiith formic acid decomposes the 
geraniol into tcrpencs and similar compounds, the citronellol alone 
being esterified. 

C. T. Bennett (P, cO E. 0. B., 1921, 351) has exammed this 
jDrocess criticalhg and finds it to be unreliable. 

The estimation of citronellol bj' heating for one hour on a 
water bath with twice its volume of formie acid (100 per cent.) 
was finst proposed bj’ Walbaum and >Stephan {BericJiie, 1900, 33, 

The method was subseciuentl}* used b^y 3Icssrs. SclnmmGl cb Co. 
for the estimation of citronellol in otto of rose {ScliimmeVs Reporls, 
i^pril, 1901, and October, 1904). The results of several determina- 
tions b^’ tliis method were imblishcd in the Perjumcry ami Essential 
Oil Record, 1913, p. 32S, and for comparative purposes it was 
assumed to be a useful factor. The determination of citronellal 
b 3 ’’ the same method has been recommended b 3 ’' Scliimmel tb Co. 
(“Volatile Oils,” vol. i., p. 581). Simmons, however (P. cb E. 0. R., 

1913, p. 297), showed that the x^’oeess does not give accurate 
results. Kot onl 3 ' does it fail to completch’’ convert geraniol into 
terpenes, but it gives high results with jmre citronellol. These 
facts were confirmed b 3 '’ subsequent exiDeriments (P. <b E. 0. P.-, 

1914, p. 51), when it was shown that a pure citronellol estimating 
99'7 per cent. b 3 * acet 3 ''lation indicated 119-S per cent. b 3 ^ the 
formic acid method. 

In order to further test the method by var 3 dng the conditions, 
the following experiments have been conducted in the anal 3 dical 
laboratory of Messrs. Wright, La 3 unan and Umney, Ltd. : — 

Indicated percentage 
' of citroncHoI. 

Experiments on pure citronellol. 

Heated for one hour on water bath vdth 

an equal volume of formic acid . . 99'7 

Digested for one hour at 20° C. . . 108*7 


P E P F U M E R 1\ 

Indicated percentage 
of citronollol. " 

Experiments on j)ure geraniol. 

Heated for one hour on water bath . . 46-8 

Digested for one hour at 20° 0. . . 82'2 

Experiments on equal weights of geraniol and 

Heated for one hour on water bath . . 29’0 

Digested for one hour at 20° 0. . . 68*8 

Experiments on citronellal. 

Heated for one hour on water bath . . 43*8 

Heated for tu'o hours on water bath . 33-1 

Digested for one hour at 20° C. ... 76-0 

Experiments on equal weights of citronellal and 

Heated for one hour on water bath . . 29*0 

Digested for -one hour at 20° C. . . 68*8 

Experiments on Burmese citronella oil. 

Heated for one hour on water bath . . 34-6 

Heated for two hours on water bath . 30*3 

Digested for one hour at 20° C. . . 68*2 

Digested for one hour in freezing mixture . 69'2 

Citronellal by absorption with 35 per cent. 

sodium bisulphite solution ... 52 

These results show that the formic acid method is unreliable 
for the determination of either citroneUol or citroneUal. These 
conclusions are confirmed by A. St. 0. Pfau [Jour. PraJet. Chem., 
1921, 102, pp. 276-282), who finds that the method gives inexact 
results, in part because a portion of the geraruol is converted into 
the formic ester. With pure citroneUol the author’s results were 
irregular and high when 100 per cent, acid was used, and low vdth 
a weaker acid. The action of the 100 per cent, acid yields a 
mixture of products containing unchanged citroneUol, a smaU 
amount of volatUe Uquid which is possibly an aliphatic or cycUc 
terpene, citroneUol formate (boiUng point, 99° to 100° at 7 mm.), 
the compound C(CH3)20H [CH2]3CH(CH3)CH2CH20CH0 (boiling 
point, 129° C. at 5 mm.; specific gravity, 0'9651 ; optical rotation, 
1° 46' ; refractive index, 1*4488), and the corresponding diformate 
(boiUhg point, 140° to 141° at 7 mm.). 

G. T. B. 

ALCOHOLS, HIGHER FATTY.— The higher fatty 
alcohols are quite analagous to the higher fatty aldehydes {q.v.), 
but are so expensive and so unsatisfactory, unless absolutely pure, 
that they are not largely employed in perfumery. The alcohols 
from 8 to 12 carbon atoms — as they are usually described — have 


p ]<: p F u M F n 1 

(loraJ odoura of a iiondescripl cliaraclcr, the 3 2 carbon body 
recalling the odonr of lily of fhc valley. According to Prins 
(P. cb E. 0. P., 1917, G 8 ), octyl alcohol (specific gravity, 0-8278 ; 
boibng point. 197*^) lias a useful rose odour. It also recalls 
opoponax. Decyl alcohol is useful in iireparing flower odours of 
the ro.'=:e typo. Their emjiloyincnt is confined to rounding off 
floral odours. An American perfumer has described decyl alcohol 
as “ an alcohol which the up-to-date manufacturer uses to deceive 
the co]uer of odour.s." (See under the respective alcohols.) 

ALCOHOL, ISOPROPYL.— Isopropj-l alcohol or dimethyl 
carbinol is now licing employed to some extent in perfumery, 
owing to the prohibitive duty on ordinary or ethyl alcohol. 
Isopropyl alcohol has the formula CH(OH)(CH 3 ) 2 . When pure 
it is a colourless and nearly odourless liquid of specific gravity 

0 - 789 at 2 UL and boiling at 82^ to 83°. Its refractive index is 

1 - 3749 at 20 '. For perfumery purposes it should be as odourless 
as possible, otherwise it is q^iite useless. It is obtained by 
numerous reactions, such as that between isopropyl iodide and 
lead hydi’oxidc. 

It is sold under various fancy names, and various methods for 
its preparation industrially have been described. For example, 
C. Ellis, of New Jcr.=ey, describes a method depending on the 
absorption of the gases from the cracking of petroleum by sul- 
phuric acid of specific gravity 1 - 8 . These gases arc very rich in 
propylene, which combines with suljfiiuric acid to form an alk}’! 
sulphonic acid which is hydrolysed into the corresponding alcohol. 
For its comparative harmlcssncss, vida .D. H. Grant, Aniencan 
Journal of the Medical Sciences, August, 1923. 

ALDEHYDES.— The aldehydes form one of the most impor- 
tant groups of the constituents of essential oils, and also of the 
more generally employed artificial perfumes. The aldehydes are 
characterised by containing a —CO— group which is combined 
with one allcyl radical and one hydrogen atom, thus, R' — CO— H, 
ethyl aldehyde, for example, being CHg — CO— H. If the — CO — 
group is attached to two alkyl radicals, the body is not an aldehj dc, 
but a ketone, thus, acetone CH 3 — CO — CH 3 . 

Aldchr’des. in general, may be produced by the oxidation of 
primary'alcohols {vide Alcohols ”), or by the distillation of the 
barium or calcium salt of the corresjjonding fatty acid with 
barium formate, thus : — 

(R.COO) 2 Ba -4- (H.COO)oBa = 2 BaC 03 + 2 R.CO.H 

Bf^rium salt Barium formate Barium carbonate Aldehyde 


P E P F U M E P 1’ 

Tt is often necessary to characterise aldehydes for the purposes 
of identifieation. The following arc the most important of their 
crystalline comj)oundSj which can be prepared and their melting 
j)oints determined for the purpose. 

(n) Semicarhazoncs . — Most aldehydes form a crystalline com- 
pound with semicarbazide ; the condensation products are knoAvn 
as semicarhazoncs. and are u.sually crystalline bodies of sharp 
melting point. They are formed according to the following 
ci’cation : — 

R.COH -i- NHo.NH.CO.NI-L = R.CH : N.NH.CO.NH, ^ H„0 

Altlcliyd'j Rcmicnrbazitic Konilcarbazonc 

They are obtained by dissolving the aldehyde in alcohol, adding 
excess of a mixture in equimolecular proportions of semicarbazide 
hydrochloride and acetate of sodium. The mixture is allowed to 
.stand for several hours, and water is then added. The precipitated 
semicarbazones are recrystallised from methyl alcohol. 

ib) Oximes . — ^Nearly all aldehydes form ciystalline oximes by 
combination with hydroxjdaminc according to the reaction — 

R.COH -L NHoOH = R.CH : KOH -h H„0 

Aldehyde Ilydroxylainlne Oxime 

Equimolecular quantities of the aldehyde and hydroxylamine 
hydrochloride are dissolved in alcohol, and sufiicient alcoholic 
solution of potash added to liberate the hydrox 3 'lamine. The 
whole is heated on the water bath for sixW minutes. 

(c) Phenylhydrazones . — Most aldeh^’des combine with phenjd- 
h 3 ’'drazinc to form phenj^Uydrazones, most of which arc crystalline. 
Thej’- are formed according to the equation — 

R.CHO -f RHo.NH.CcIis = R.CH : N.NH.CJds + HoO 

Aldehyde riicjiylhydrarinc Jdicnylhydrarono 

Thej' arc prepared by heating the aldehyde in alcohol, under a 
reflux condenser, with phenjdhydrazine hydrochloride and sodium 
acetate for an hour. 

Other compounds will be referred to where necessaiy under 
particular aldehydes. {Vide “ Aldehj’des, Determination of,” and 
“ Aldelydes, Higher Fatty.”) 

tion of aldehydes is one of the operations which the analyst has 
to undertake most frequent^ to decide upon the value of ra^v 
materials for the perfumer. In such oils as lemongrass, cassia, 
cinnamon, and lemon the estimation of the aldehydes is the 
determining factor as to the value of the oil. 

The most general process in use amongst analj’-sts depends on 


P E P F U M EP y 

the fact that most aldehydes possess the power of forming com- 
jDOunds %nth sodium bisulphite or sodium sulphite wliich are 
soluble in water. In general, the processes used for the determina- 
tion of aldehydes depending upon this fact are equall}^ applicable 
to the determination of ketones. The following processes are of 
general appheation to most of the aldehydes and ketones : — 

{a) Bisul'phite, of Sodium Process. — ^Five cubic centimetres of 
the oil in which the aldehj’-des are to be determined are placed in 
a flask holding alrout 150 to 200 c.c., with a long neck which is 
graduated in c.c. To this is added 50 c.c. of a hot 30 jDer cent, 
solution of sodium bisulphite, and the whole well shaken. The 
flask is placed in a boiling water bath and is repeatedly shaken, 
with the gradual addition of more bisulphite solution, until all 
crj'stals formed have disappeared and a clear oily liquid rises to 
the surface. The shaking should be repeated and vigorous, and 
the process should last from an hour (lemongrass oil) to two hours 
(cassia oil). More bisulphite solution should be poured in, up to 
nearly the top of the neck, and the flask stood aside for twenty-four 
hours to allow the whole of the rmabsorbed portion to rise into the 
graduated neck. As the specific gravity of both the absorbed and, 
unabsorbed constituents do not differ greatly, the calculation by 
volume is m juactice accepted as accurate. So that if 4 c.c. have 
been absorbed by the bisulphite and 1 c.c. rises into the neck of 
the flask, the oil is returned as containing 80 per cent, of aldehydes. 

(&) Neutral SuIjFPte Process. — The determination is carried out 
exactly as in the case of the bisidphite process, except that the 
absorbing solution is one of neutral sodium sulphite and the end 
of the process is controlled by a definite reaction; A few drops of 
phenolj)hthalein solution in alcohol are added to the contents of 
the flask, and a red colour is soon developed in the flask due to 
the liberation of free aUcali during the process. A few drops of a 
10 per cent, solution of acetic acid are added till the colour 
disappears, and the shaldng repeated. This is done so long as the 
red colour develops, and when no return of the colour occius after 
ten minutes the absorption is complete, and the result is read off 
in the neck of the flask after twenty-four hours. 

(c) Hydroxylamine Method . — ^The fact that aldehydes form com- 
pounds with hydroxjdamine was first utilised by Walther [Pharm. 
Central., 1899, 40, 621) for the quantitative determination of this 
group of bodies. The original process, shghtty modified by A. H. 
Bennett, is practically universally used for the determination of 
citral in lemon oil and similar oils wfliere only small quantities of 



aldehydes are present. Twenty cubic centimetres of the oil are 
mixed with 20 c.c, of seroinormal hydroxylamine hj’^drochloride 
solution (in 80 per cent, alcohol), and 8 c.c. of normal alcoholic 
potash solution and 20 c.c. of 90 per cent, alcohol are added. 
The mixture is gently boiled for thirty to forty-five minutes under 
a reflux condenser, and then allowed to cool. The condenser is 
washed down with water, and the contents of the flask brought 
up "to about 250 c.c. with water. A blank experiment is carried 
out vdthout the oil. A few drops of phenolphthalein are added 
and the mixture neutralised to tliis indicator 'with alcoholic potash 
solution. Methyl orange is then added and the mixture exactly 
neutralised to this indicator vith seminormal sulphuric acid. 
The end reaction is not easy to determine, so that the method of 
spotting on a white tile vdth drops of the indicator is resorted to. 
Each cubic centimetre of seminormal acid is equivalent to 
0-076 gram of citral (or the equivalent quantity of any other 
aldehyde), so that 20 c.c. of the oil (calculated to weight by 
multiplying by the specific gravity) contains 0-076 x a; grams of 
citral, where x is the number of cubic centimetres of seminormal 
acid consumed. 

Eurther methods of special application will be found under 

Citral. (Vide also E. J, Parry, Chemistry of Essential Oils, 
etc,, vol. ii., Scott, Greenwood & Co., London ; and Bennett and 
Bateman, P. c6 E. 0. P., 1923, 268.) 

ALDEHYDES, HIGHER FATTY. — ^During the past few 
years a most -valuable addition to the perfumer’s art has been 
made by the manufact'ure on a commercial scale of the higher 
aldehydes of the so-called fatty series. As a group these bodies 
possess an extraordinarily powerful odour, of a fruity nature, which 
is so po'^verful and persistent that a single drop spilt on one’s 
clothes renders one sufl&ciently odoriferous to be objectionable. 
They must be used with great discretion and in minute quantities, 
as otherwise the great improvement effected in a floral odour by 
them use tends to pass to an objectionable and penetrating strength 
which spoils the whole bouquet. Properly blended and used with 
discretion, they are of the highest value to a perfumer wdio wishes 
to ‘‘create” his own proprietary bouquets. They are^equaUy 
of value m the rounding off of fruit essences. The following are 
the^ principal of these peculiar aldehydes, which, on account of 
their proneness to oxidise, are frequently* sold, in 10 per cent, 
alcoholic dilutions, which are very convenient for use in measuring 
out very minute quantities. 


p E n F u M E Ji y 

Ileplylic Aldehyde, CH 3 (CH 2 ) 3 .CHO. — Tliis body is also known 
as oenanth^dic aldcln’dc, and is prepared by llic dry distillation 
of castor oil under a pressure of 100 mm. Only small quantities 
can bo dealt with at a time. It may also be prepared by “ esteri- 
fying ” castor oil by methyl alcohol j using hydrochloric acid as 
the condensing agent and distilling in vcicno. When the tempera- 
ture rises to 250^ at 12 mm., no more is distilled, as the residue is 
more or less unaltered castor oil. The aldehyde is accompanied 
l)y metlqvl undccylenate. and can be separated by means of its 
bisulphite compound. It is an oil of strong fruity odour, boiling 
at about lo2'’. and having a specific gravity 0-S20 and I’cfractivc 
index 1-4150. 

Ociylic Aldehyde, CH3(CH2)c^'^^0- — eight cai’bon 
aldehyde, and is found naturally in ncroli and rose oils. It is 
of considerable value in perfumes of the rose, jasmin, geranium, 
neroli and orange types. The starling point of this bodj^ is 
cocoa-nut fat. The fat is saponified, an<l the fatty acids separated 
1)3' the addition of dilute sulphuric acid. The aqueous liquid is 
extracted with petroleum ether, to obtain the fatty acids soluble 
in water, and these are added to the previously* separated fatW 
acids. The principal fatty acids ])rc.sent are caprylic and lauric 
acids. These arc jiow washed with a little water, dried over 
anhydrous sodium rsulphatc. and heated under a rcfiux condense)’ 
for six to cicht hours with their own weight of methyl alcohol and 
a small amount of sulphuric acid. Water is then added, and the 
oil sej)arating is washed with water and then with dilute alkali. 
The esters so formed are then fractionated in vacuo, the earlier 
runnings containing most of the methyl caprydate, whilst the later 
runnings contain the methyl laurate. 

The methyl caprylatc is reduced by sodium and alcohol, and 
yields octyf alcohol CH3(CH2 )c.ChJ 0H. This body is then 
converted by a controlled oxidation into octylic aldehyde. It is 
a liquid of powerful fruity odour, having a si)ecific gravity 0-S27, 
refractive index T4105, and boiling point 82° at 13 mm., or 175° 
at 7 GO mm. 

Nonylic Aldehyde, CH 3 {CH„) 7 .CHO, is the nine carbon aldehyde 
of the series, and occurs naturally' in both rose and orange oils. 
It is used in the same manner as octylic aldcliyvle. It is an oil of 
specific gravity' 0-S277, refractive index 1*4245, and boiling 
point 92° at 13 mm. Its melting point is from + 5° to -}- 7°. 
It is prepared as follows : Undecydcnic acid, one of the products 
of the dry distillation of castor oil, is carefully melted with caustic 



potash and water until no more hydrogen is given off. The mass 
is exhausted with water, and dilute sulphuric acid is added to the 
aqueous extract. This precipitates pelargonic acid, which is 
esterified ndth ethyl alcohol in the usual manner. The ethyl ester 
is reduced by sodium and alcohol to nonylic alcohol, which, by 
controlled oxidation, jdelds non 3 dic aldehyde. {Vide also Levdn- 
sohn, P. t& E. 0. R., 1924, 12.) 

P. Bagard [Bull. Soc. Chirti. (4), 1, 346) has prepared nonj^lic 
aldehj'de b}’" the dry distillation of a-hydroxycapric acid, which 
he obtains b}’’ starting from pelargonic acid and passing tlmough 
the intermediate stage of capric acid by means of the reactions — 

^CHg— (CHa),— COOCoHs 

CH3— (CHo)-— COOH- 

Pelargonic add 

->CH3— {CHa)^— CH3— CISWCH3— (CH2)7— CHa— COOH 

_ Cajiric acid 

(CHa)7— CHBr— COOH 

->CH3— (CHa) 7— CHOH— COOH 

a-IIydroxycapric acid 

The same author has obtained decjdic aldehj^de b}'- the distilla- 
tion of a-hj^droxjmndecjdic acid prepared from undecylic acid, 
which is itself obtained from undecjdenic acid. 

The characteristic derivatives of these aldehydes described by 
Bagard (for their preparation, see the original paper) are ; the 
semicarbazone of nonylic aldehyde, melting point 100° C. ; the 
oxime of nonjdic aldehyde, melting point 64° C. ; the oxime of 
decylic aldehyde, melting pomt 69° C. : the azine of decylic 
aldehyde, melting point 34° 0. {Roiire-Berlrand Fih, Bulletin 
Maj’-, 190S, 44.) 

Decijlic Aldehyde; CH 3 (CH 2 ) 8 .CHO, or the ten carbon aldehyde 
of the series, is prepared in the same manner as nonyHe aldehyde, 
starting from capric acid instead of pelargonic acid. It is most 
useful in the. reproduction of the odours of violet, orris, neroli, 
cassie flowers, rose and orange. It is probably the most general^ 
used of the series so far as perfumers are concerned. It is an oil, 
boiling at about 212°, of specific gravity about 0-828 to 0-834, 
and refractive index 1-4298. (See above, under “ Nonvlic 

Undecylic Aldehyde, CH 3 (CH 2 ) 9 CIIO, is the eleven carbon 
aldehyde of the series. This aldehyde is made from the method 
ester prepared from the crude lamic acid of cocoanut fat, as 
described under Octylic Aldehyde ” above. The methyl lam-ate 
is saponified in the usual manner, and the resulting lauric acid is 

31 . 

p }<: li F V M p: li y 

degraded according to tlic method of Blaise. It is treated with 
PCI 5 , wliich transforms it into lanryl chloride, which is brominated 
and the rcsnlting compound hydrolysed to bromo-laurie acid. 
This is convej’tcd into oxylauric acid Ijv means of caTistic alkali. 
Oxylanric acid is directly converted into undecylic aldehyde by 
heat. This aldehyde, which has an intense floral and fiaiity odour, 
boils at 117' to 118^ at 18 mm. It has a specific gravity 0*825 at 
23'. a 7 id I’cfractive index 1--1320. 

AJdcJii/dc, CII;,(CT]n)]oC'nO, or laui'inic aldehyde, was 

riginally recommended for blending with violet ])erfumes, but is 
not well adapted to this ])urpose. Jt results from the reduction 
of ethyl lauratc by sodium and alcohol, and controls oxidation 
of the resulting alcohol. It is a solid ])ody, melting at 44° to 45 °, 
boiling at 185° at 100 mm., and rajudly oxidising to lauric acid. 
It should therefore be ke])t in alcoholic solution. 

Tndcnjl AhPlnjdc, CH..(CTTo)jjCIIO. — This aldehyde has no 
distinctive flower perfume, but is exceedingly powerful, and can 
be used in most floral perfumes. American perfumers state that 
it has licen used with great .success by those wishing to ei’oate 
special bouquets. 

Tctradccvl and hexadccvl aldehvdes. containing 14 and IG 
atoms of carbon rc.spcctively, have intense odours, the former 
recalling peach, and the latter strawbcriy. Psed in extremely 
minute quantities they arc of great value to the perfumer, but 
if the quantity exceeds mere traces the composition is ruined. 

Ilcxjilcnk Aldehyde., CH.vCIL.CHo.CK : CIl.CHO. i,s an un- 
saturated aldchvdc of the fat tv scries. It has an odour recalling 
those of vine and strawbeny leaves. 

(Refer to Wcyl. *' IMethodcs dc chcmic organique ; aiid to 
Ullmann, “ Enzyklopcdie d. tech, chemie,” voi. 0.) 

A* VJr* 

ALECTORIA. — This i.s one of the lichens growing on oak and 
other trees from which the extract known as mousse dc chenc or 
oak moss is manufactured. The perfume obtained is not so fine 
as that from other lichens such as Fvernia .'species. 

ALLSPICE. — ^Allspice or pimento consists of the ' dried 
unripe fruits of Eugenia ■pimcnla [Pimenfa officinalis, Lindlcy), a 
plant belonging to the natural order Myriacecc. The sxncc takes 
its name from its resemblance in perfume and flavour to a mixture 
of cinnamon, cloves, and nutmeg. It is sometimes known as 
Jamaica pepper. 

The plant is a native of the West Indies, found on calcareous 


soils near the coast in Cuba, Hayti, Trinidad, Domingo, and 
various islands of the Caribbean Sea. The chief part of the 
world’s supply, however, comes from Jamaica, Mexico, Costa 
Rica, and Venezuela also produce some of the spice. The fruit, 
after gathering, is carried in baskets to the barbecue, a paved 
court divided into compartments by a low sill so that the berries 
of different days’ gathering may be kept separate. They are 
spread out in the sim and turned over with a wooden rake so as 
to expose them thoroughly to the sun. They take from three to 
twelve days to drj^, and must be well protected from damp, 
which damages them materially. The average annual output 
from Jamaica is about 11,000,000 lb. [Vide Ridley, "Spices,” 
Macmillan & Co., London.) 

The berries yield from 3 to 4-5 per cent, of essential oil on 
distillation, wliich contains a large proportion of eugenol. It has 
the following characters : specific gravity, 1-024 to 1-056 ; optical 
rotation, —0° 40' to — 5° ; refractive index, 1-5250 to 1-5350 ; 
and eugenol value, 65 to 80 per cent. It is soluble in twice its 
volume of 70 per cent, alcohol, with, at most, slight turbidity. 

The oil distilled from the pimento leaves is also rich in eugenol. 
Experiments on a considerable scale are being carried out by the 
Department of Agriculture of Jamaica with a view to marketing 
the oil for the extraction of its eugenol for vanillin manufacture. 
The leaves jneld from 0-4 to 1-2 per cent, of oil, usually containing 
from 85 to 92 per cent, of eugenol, although the leaves from the 
Walderston district often 3 neld oils of much lower eugenol value. 
The departmental chemist, Mr. E. E. A. Campbell, considers that 
distillation by means of dry steam under pressure is the best 
method to be adopted, and he does not consider that the addition 
of salt to the water in the stills is of any special value. 

ALLYL - PULEGON E. — ^Haller and Ramart [Gomptes 
Rendus, 1924, 179, 120) have prepared a number of allcyl-pulegones 
from the pulegone obtained from American pennyro 3 ’’al oil. They 
describe it as having an odour resembling those of ionone and 
oil of vetivert, and consider that it may have a commercial 

(OH).C 6 ll 4 , is prepared by heating under a refiux condenser a 
mixture of equal parts of sahcylic acid and aUyl alcohol with a 
little sulphuric acid. It is a liquid of floral and fruity odom-, 
boiling at 247°. It is not used much in perfumery, but has been 
r- 33 3 


rcconiinenclGd for modifying flower odours {Bgv. GJicm. Ind.^ 1911, 
p. 129). 

ALMONDS, OIL OF. — ^An essential oil is obtained from tlie 
kernel of the bitter almond, Pnmvs amygdahis, which is identical 
with that obtained from either j^each or apricot Imrncls. Tlic.5C 
oils are so nearly identical that for all practical purposes they aie 

Bitter almond oil docs not exist as such in the kernels, hiit 
results from the action of water on a glucosidc, amygdalin, uhich is 
present, under the influence of the ferment, cmulsin, which is also 
present. In commerce the fixed oil is expressed, and the press 
cakes are ground up and soaked for twenty-four hours in water 
usually containing some salt. The essential oil is by this time 
fully developed, and is then distilled. The glucosidc on decompo- 
sition yields dexti-ose, henzaldchyde, and hydrocyanic acid. The 
essential oil consists almost entirely of henzaldchyde, with se\eial 
per cent, of the highly poisonous hydrocyanic acid. Fiiis is 
removed in various ways ; for example, by mixing the oil with 
water, red oxide of mercury, slaked lime, and feiious chloiidc, 
out of contact with the air, and heating it on a water hath. The 
hydrocvanic acid is decomposed, and the rectified oil now consists 
of nearly pure henzaldchyde. 

As hydrocj’anic acid is a very deadly poison, it is of the liighest 
importance to see that it is free from any traces of the acid. Such 
oil is sold as “ S.A.P." {sh\e acid. 2 '>rvssic.). In order to test for this, 
a few' drops are dissolved in alcohol and a few drops of solutions 
of ferric chloride and ferrous sulphate arc added. A slight excess 
of caustic soda solution is then added, and the precipitate formed 
is dissolved in pure hj'drochloric acid. A deep blue coloui oi 
precipitate (prnssian blue) appears if traces of hydrocyanic 
(prussic) acid arc present. 

A pure hitter almond oil free from prussic acid has a specific 
gravity 1-049 to 1-055, refractive index 1-5420 to 1-54G0, and 
boiling point 179°. 

The oil requires careful preservation away from air and light, 
especially if it contains traces of w’ater. It is liable to oxidise - 
rapidly if not so preserved, with the formation of benzoic acid. 

This is determined by titration w'ith ^ caustic allcali, and should 

not, in good sanijiles, exceed .1 per cent. 

The old adulteration of almond oil with nitrobenzene is now 
quite apocrjqihal, the onfy adulterant used in actual practice 



being artificial benzaldehyde [q.v.). If the latter body contains 
more than the merest trace of chlorine -(which is introduced during 
the process of manufacture), it is not suitable for perfumery 
purposes, since it tends to darken any pale substance, such as 
white soap, which it has been added to. But if the artificial 
benzaldeh 3 ’-de be absolutelj’- pure, it forms an excellent substitute 
for the natui’al oil, at a veiy much lower price. 

It is usual to saj’- that the natural oil is a trifle more delicate in 
odour, but this is veiy doubtful, and as a largo proportion of the 
oil sold as natural is, in fact, ahnost, if not quite, entu’cly artificial, 
the perfumer is recommended to paj'- attention to the artificial 
benzaldelyde or to purchase the natural oil from recognised actual 
distillers of reimte. {Vide " Benzaldelyde.”) 

ALOE WOOD.— FuZe “ Linaloe oil.” 


ALPINIA OILS. — ^The fresh roots of Alpinia Malaccensis 
yield about 0-25 per cent, of essential oH containing methyl 
cinnamate. It has a specific gravity 1‘039 to 1'047 at 27° ; 
optical rotation, -j- 0° 15' to 1° 30' ; refractive index, 1*5477 ; 
and saponification value, 256 to 278*5. The leaves, accorduig to 
van Romburgh {Ko7i. Alcad. Weten. Amsierda7n, 1898, 550), yield 
0*16 per cent, of essential oil containing pinene, and 75 per cent, 
of metlyl cinnamate. Its specific gravity is 1*020 at 26°, and 
optical rotation + 6° 5'. Ultee {Amialen, 1914, 405, 175) 

exammed the oil from Alpinia Galanga and found it to contain 
50 per cent, of methyl cinnamate and 20 to 30 per cent, of cineol. 
The oil had a specific gravity 0*974 to 0*985 ; optical rotation, 
+ 4° to -{- G° ; and refractive index, 1*5164. Gardies {La Par- 
fumerie Moderne, 1923, 109) has reported on an oil from Tonlcin, 
known as Beio-Rieng, which possesses a fine odour of an infusion 
of tea. It is possibty an Alpmia oil. It has a specific gravity 
0;902 ; optical rotation, +8° 8' ; refractive index, 1*4884 ; 
esters, 3-8 per cent. ; and free alcohols, 33*8 per cent. 

AMBER, ARTIFICIAL. — The so-called artificial ambers 
or “ ambres ” are merely mixtures of heavy odour-bearing 
substances together with (usually) animal fixatives. For example, 
musk, civet, castor, mousse de chene, balsams of Peru and Tolu, 
storax and cinnamic esters enter into their composition. The 
odour is generally far more pronounced than that of ambergris. 
A nitrated dibromo-butyl-?n-cresol methyl ether, melting at about 
100°, has been suggested as an artificial amber. 

36 3 _. 


AMBERGRIS. — ^Ambergris is an exceedingly valuable raw 
material of perfumery, as are several other animal products ; it 
is also very expensive. It is an opaque grey, yellowish, or black 
material, occurring in lumps of all sizes, the largest piece yet 
recorded being one weigliing about 200 lb. It is found on the 
sea coast or floating on the sea near the coasts of India, Afiica, 
and Brazil. About thirty years ago a large proportion of the 
ambergris sold on the London market was collected by the whalers 
of Tasmania and New Zealand who phed their trade in the 
Antarctic Ocean. The industry has now ceased to exist so far as 
Tasmania is concerned, but the New Zealand flshermen occasion- 
ally bring in some ambergris. As this substance has been 
surrounded by mystery for many years, it will be of interest t;o 
briefly note the following views which early writers have expressed 
as to the actual origin of ambergris. An early writer, named 
IQobius (“ Perfumery ” (E. J. Parry), Sir Isaac Pitman & Sons, 
Ltd., p. 73), gives, amongst others, the following views which have 
been entertained as to its origui ; — 

(1) It was beheved to be the excrement of a bird, eommon in 
Madagascar, melted by the sun’s heat, washed out to sea, 
swallowed by a whale, and passed through its body unaltered. 
(2) Others believed it to be excrementary material of certain 
cetaceous animals. (3) It was siumised to be a wax or gum 
exuding from certain trees growing on the sea shore, which dropped 
into the sea, congealed, and so became ambergris. (4) A common 
idea m the Orient was that it sprang from the bed of the sea as 
naphtha does from the earth, or that it was a kind of bitumen 
gradually working up from the ocean and hardening in the sun. 
(5) By some it was held to be a kind of marine fungus torn up 
. from the bottom of the sea by violent tempests. (6) The origin 
of ambergris was also ascribed to honeycombs which had fallen 
into the sea from rocks where bees had built then nests. (7) Dr. 
Boylston and Mr. Dudley [PMl. Trans., 385, 387) asserted that 
ambergris was an animal concretion found in balls in the body of 
the male sperm whale. (S) A certain Herr Neumann, chemist to 
the King of Prussia {Phil. Trans., 433, 434, 435), denied that 
ambergris was an animal product at aU, and that, if it were found 
in whales, it must have been first swallowed by them. His own 
opinion was that it was a species of bitumen exuding from the 
earth hito the sea. An old scientific v,^ork of the eighteenth 
century states ; “ The pieces are frequently seen composed of 
divers strata . . . with stones and other bodies enclosed within. 


r E M U M E K X 

and tlie strata are sometimes full of little shells . . . whence it 
maj'- he conjectm’ed that the ambergris had originally been in a 
fluid state . . . and enveloped such bodies as happened to he in 
its way.” 

Ambergris is now definitely known to be a pathological secretion 
of the sperm whale PJiyseier macrocepliahis. Sometimes the whale 
manages to reject the secreted ambergris, and then recovers from 
his disease ; otherwise he dies. As a rule, the dead body is eaten 
hj’ fish and the ambergris liberated, when it may be found floating 
on the water or may he washed ashore. If a sick whale is caught 
ahve, the whalers may make more out of the ambergris than out 
of the whole carcase. 

Jean Gattefosse, in' an article on ambergris {La Parfmnerie 
Moderne, 1920, 259), gives the following as the method by which 
ambergris is secreted by the sperm whale. The odorous con- 
stituents of ambergris, in his opinion, exist already formed in 
certain cejihalopods such as Elodone moschata, upon which the 
whale prej'-s to a very considerable extent. In normal circum- 
stances these substances, as well as the crystalline ambrein, are 
expelled in the fceces. But if the whale be sufiering from a certain 
micro-organic intestinal disease, these bodies are not expelled. 
The lumps of ambergris are then formed by the crystallisation of 
the ambrein with other matter, as those substances not concerned 
in the formation of the calculi are consumed by the bacteria. The 
lumps are then expelled fortuitously or, if not, result in the 
animal’s death. 

According to V. Hasslauer {La Parfimerie Moderne, 1921, 56), 
ambergris is a calculus formed in tire sperm whale by the un- 
digested residues of its food, combined vdth biliary and gastric 
juices, blood, and sometimes faecal matter. The calculus, when 
found in the interior of the animal, is not of the same quahty as 
that which is expelled. The sperm whale is very migratory, going 
far afield in search of his food. It furnishes ambergris varjdrrg in 
character according to where it is caught, thus indicating that 
the natine of the food influences the character of the ambergris. 
Hasslarrer claims that it is possible, from the odour and aspect of 
the ambergris, for an expert to say from what part of the world it 
comes. Ambergiis which has been expelled and exposed to the 
sun for several years is certainty of the finest quality. 

Some excellent work on the formation of ambergris was com- 
menced by Bauregard (“ Les cr 3 'ptogames de I’ambre gris,” Ann. 
de mierograpMe de Miqnel, 1898). He separated an organism, 



whicli he caUcd Sjnrilhts racli PhjsGieris, from the intestines 'of 
the animal -which appeal’s to he responsible for slowly attacking 
the faecal matter and thus contributing to the formation of the 
calculus. His regretted death stopped this very promising 

The value of ambergris in perfumery lies in its very high fixative 
jDOwer, coupled with a slight animal odour, which has always been 
an attraction in the most refined perfumes so long as it is not too 
highly accentuated. In common with other animal perfumes, it 
has m some quarters held a reputation as an aphrodisiac, but this 
is quite without foundation. 

It occurs in characteristic lumps of grey to greyish-yeUow or 
black coloiu’, vith a characteristic odoiu’ and a somewhat greasy 
surface. It has a specific gravity of about 0*900 to 0*920 and 
softens at about 30°, melting at about 40°. 

The exact composition of ambergris is not known. Pelletier and 
Caventou (“ Traite de chemie,” 1805) claimed to have isolated a 
substance which they term ambrein from it, and Chevalier, in 
1828, again separated it. In 1912 Eiban found that tliis was a 
mixture, but by repeated recrystallisations he isolated a pure bodjq 
for which he retained the name ambrein, and which melts at 82°. 
Traces of aromatic acids and of an essential oil arc also present. 
The actual odour bearer has not yet been definitel}'- characterised. 

Ambergris is used in perfumer}’- m the form of an infusion in 
90 per cent, alcohol, usuaUj’- of about 5 per cent, strength. It is 
usual to macerate with regular shaking for a period of from-one to 
three months. 

Artificial ambergris and similar preparations have no relation- 
ship vdth the natural substance, but are merely ‘‘ imitation ” 
ambergris, having an entirely different odom’, but which are 
useful as fixers and contribute to the “ hea-vy ” type of odour. 

The P. cfc E. 0. R, (1922, 300) gives the follovdng details of 
the examination of true and false ambergris by H. I. Cole, of 
the Bureau of Science, klanila : — 

In 1912 Riban [Com^ites Rendus, 1912, 154, 1729-1732; Bull. 
Soc. Cliem., 1912, iv., 11, 754-757) investigated ambrein more 
closely. He had come into possession of a small quantity of 
ambrem wliich had, in the course of time, separated out from the 
alcoholic fiquid in a bottle contamuig extract of ambergris. The 
substance, after being recrystalhsed from alcohol, melted at 
between 82° and 86° C. It is a wMte crystalline sohd separating 
from its alcoholic solution in slender needles. Combustion showed 



it' to^ possess the formula CagH^oO. The compound tends to 
remain in the superfused state when melted, even if sown with 
crystals. When warm and dry, it becomes highly electrified on 
slight rubbing. It is not optically active, has a neutral reaction, 
and is insoluble in water, but soluble in most organic solvents. 
When acted oh by bromine in carbon tetracliloride solution, it 
gives an octo-bromo derivative OogHgoOBrs, a white vitreous 
solid. ^ Chlonne, under similar conditions, decomposes it. On 
warming ambrein with phosphorus pentachloride, a wliite amor- 
phous mass of pentachloro ambrein CggHggClgO is obtained. 

The physical constants of ambergris as given in literature 
vary widely. No chemical methods for its identification are to 
be found, m the literatme available; The Chinese test its purity 

by scraping it upon boiling tea, in which they consider it should 

A number of substances suspected of being ambergris have 
been submitted to the Bureau of Science for identification, but one 
in particular is so generally considered to be the genuine article as 
to deserve the name “ supposed ambergris.” This substance is 
usually found floating far out at sea in localities known to have 
gelded ambergris; It is picked up by fishermen and sold to the 
Chinese and Moros as ambergris. It has been shipped through 
the Custom House of Manila to Japan, rated as “ ambergris,” and 
IS used by the natives for medicinal purposes, and by the Chinese 
and Moros probably as an aphrodisiac. In aU physical appear- 
ances It closely resembles ambergris. It occurs in the same places, 
IS found in the same quantities, and has approximately the same 
specific gravity, and a similar mottled appearance. It, however, 
has a slightly different odour, and becomes brittle on agehn^ while 
true ambergris apparently does not. Since no methods of° identi- 
fymg it positively as ambergris were available, the matter was 
referred to the Bureau of Chemistry at Wasliington. That bureau 
reported that ” there are no satisfactory methods by which it is 
possible to identify ambergris. Perfumers are in a better position 
to determme the genuineness of this material than we would be by 
ordmary analytical methods.” 

It seems therefore that ambergris is determined in a manner 
analogous to that of a good wine ; that is, it is judged by a 
connoisseur, one who recognises it by general appearance, boquet 
or odour, etc., from a physical rather than from a chemical or 
microscopical standpoint. 

Samples of the substances were sent to the leading perfumers of 






the United States and Europe "uith the request that an opinion be 
rendered as to 'whether the material was true ambergris. The 
rephes were almost unanimous against the substance being 
ambergris. At this point the facts were brought to the attention 
of Mr. Cole. It seems that ambergris often contains “ the horny 
giUs of a cuttlefish species ” (Bruff, Cliem. Ahstr., 1916, 10, 1405) 
which serves as food for the whale. A careful microscopical 
exammation proved the absence of such horny material, but led 
to the finding of occluded fragments of moss, leaves, and bark, 
so distributed as to suggest inclusion in the formation of the 
substance rather than foreign material gathered up after the 
lumps were formed. This naturally indicated a vegetable rather 
than an animal origin'. A comparison ■^dth the samples of gums 
and resms at the Bureau of Forestrj' showed the substance to 
have a close ph 3 'sical resemblance to the latex from Ariocarpus 
elasiica (“ Philippine Resins, Gums, and Essential Oils,” Ball. 
P. 1 . Bvr. .Forestry, 1920, 20, 68. Some of the ph^’^sical and 
chemical constants of this latex, and of the “ supposed ambergris,” 
v'ere determined. The results are fisted in the table on p. 40. 
The known constants of true ambergris are given for comparison. 

From the data given above and the microscopical examination 
we are led to the conclusion that the various samples of “ supposed 
ambergris ” submitted to the Bureau of Science were neither 
ambergris nor of anunal origin, but that they were originally 
derived from a tree, probably closety related to Artocarpus elasiica. 

Recently a substance which had been found in southern 
Palawan, near Balabac, by a Moro was submitted to the Bineau 
of Science for analj^sis. It proved to be true ambergris. (This lot 
of ambergris weighed 47 kg.) The material was of a waxy nature, 
bro-wn, -ufith tiny specks of white distributed through it, and there 
were also embedded in it many fragments of the chitinous part of 
the internal shell or gladius of a cuttlefish. Other cliitinous frag- 
ments, in the form of a parrot’s beak and the remains- of the 
mandibles of the cuttlefish, were also found. This chitinous 
material is identical with the “ horn}'' gills of a cuttlefish species ” 
referred to above. These fragments appear as thin dark brown, 
opaque, finel}- striated pieces of eliitin varying in thickness from 
0-04 to OT mm. No moss, bark, or other vegetable material was 
found in the sample. 

The specific gra-Mt}’- of the ambergris was 0-834 (? 0-934). The 
melting point was 65° C. The ash content was 0-21 per cent. 
After the ambergris was melted it remained as a brownish-black 



viscous mass on cooling. Attempts to crystallise the ambrein 
from alcohol v^ere unsuccessful. No cr^^stallisable product could 
be obtained upon acetylisation with acetic anhydride. 

The above data, and especially the microscopical examination, 
proved that this substance was ambergris. 

]Mr. Cole emphasises as his conclusion that a careful micro- 
scopical examination of substances suspected of bemg ambergris 
will often prove to be of greater value in the identification of 
such substances than the ordinary pliysical or chemical methods. 

AMBRETTE, OIL OF* — ^Ambrette seeds, or the seeds of 
Sibtscus A-bshuoscJiU'S, also knoAvn as musk seed, is a valued 
aiticle in perfumery. The name Hibiscus is possibly derived from 
Ibis, the stork, a bhd which is said to chew the plant. The name 
Abclmoschus is derived from tlie Arabic kahb-el-misk grain of 
musk The plant is herbaceous, growing to about 6 to 8 feet 
in height, a native of the hottest parts of India. It belongs to the 
natural order Malvacc(B, Its large yellow flowers yield small grey 
seeds vdth a pronounced odour of musk, Avhich are distilled for 
then’ essential oil. The latter is a highly aromatic liquid, of 
specific gravity 0*900 to 0*905, semi-solid at ordinary temperatures, 
the melting point varjdng with the quantity of free fatty acids 
wliich it contains. Samples of pui’e oil are sometimes quite fluid, 
qvdng to comparative freedom from palmitic acid. Farnesol has 
been identified as a constituent of the oil. Schimmel S Co. 
{Report, April, 1912, 23) distinguish between the normal oil and 
the oil depi'ived of its fatty acids, which is liquid at ordinary 
temperatures. They give the following figures for the two oils : — 

ITormal oil. 

Liquid oil. 

Specific gravity at 15° ' 

0-9088 to 0-9123 

» „ 40° 

0-891 to 0-892 

,, , 

Optical rotation 

+0° 14' to 4-1° 19' 

Refractive index at 20° 

1-47421 to 1-47646 

Acid value 

75 to 132 

0 to 2-4 

Ester value 

66 to 113 

167-7 to 180-5 

Solidif3nng point 

38° to 39° 

iSolubiiity . . . 

Insoluble in 

Soluble in 3 to 6 

10 vols. of 

vols. of 80 per 

' - 

90 per cent. 

cent, alcohol. 



P E R F U 31 E R ] 

Lalouo and Littcrcr [Roura-Bi.rtraml Flh, Bulletin, October, 
1912, IS-j) obtained the following rtgnr('‘4 for a normal oil ; — 

Bj)eciric gravil y at 





Optical rotation , . . , . -]“1° 2-1' 

Itefractive index at 90° .... l-4G-j5 

Soluble' in 1 volume of 90 ])er cent, alcohol, but 
a .stremg tur])idify is ju’oduced on the subse- 
quent addition of the same' alcohol. 

Acid value . . . . . .47-0 

Saponification value ..... I9;v3 

,, ,, of the acelylatcd oil . 2]3‘7 

ARIiMONIA. — So ’Called lirpiid ammonia, and ammonium 
carbonate arc employed to a considerable extent in tlic manu- 
facture of ])erfumed .smelling salts. “ Li<juid ammonia is a 
solution of gaseous ammonia. Xlb.. in water, with wliich it forms a 
liydrate XIl;.Oir. 'rhe stronge.-l solution of commerce has a 
specific gravity (t-880, and contains ho'G ])er cent, of KIL ])y 
weiglit. The following table gives the strength of solutions of 
ammonia of various specific gravities ; — 

S| ecific 
Liiavit V 
liV ^ 

Gr.-im- XH; in 


i Gkuiit 

XJI 3 in 

loo 5 

1 lit:o 


l.V ' 

‘ KlO 

j 1 litie 





1 ofiolulion. 



1 -] 

















; 187 






t 200 





n o . o 

^ < i »> 

' 214 






■ 227 






! 241 




0-900 ' 


1 255 









^ 121 

0-S90 i 


j 282 




0-8S5 i 


; 298 




0-880 ! 

i 1 



' 313 


Solid “ ammonia i.s commonly known as ammonium carbon- 
ate. It is actually a mixture of ammonium hydrogen carbonate 
NH.^.H.CO;, and ammonium carbamate NH.j.ISfHo’COo. It is 
prepared by heatmg calcium carbonate with a salt of ammonia. 



Commercial samples on titration should contain from 30 to 
32 per cent, of NH3. 

AMMONIAGUh!. — ^Ammoniacum' is a gum-resin obtained 
from the flowering stem of Dorema ammoniacum, a plant found in 
Persia and southern Siberia. The stem is pierced by beetles and 
the exudation induced of the milivy substance contained in the 
ducts in the cortex. The gum-resin contains from 18 to 28 per 
cent, of gum, 50 to 75 per cent, of resin, and 0-5 to 2 per cent, of 
essential oil. 

It is used to a small extent in perfumery together noth 
opoponax. The only adulterant usuall}'- found present is the 
so-called African ammoniacum, the product of Ferula tingitana, 
which maj'- be detected as follows : — 

If about 60 grains are powdered and boiled for fifteen minutes 
with I oz. of hydrochloric acid, and the liquid cooled and filtered 
and then rendered allcaline •udth solution of ammonia, pure 
ammoniacum will not show any fluorescence ; whilst if the 
African gum-resin be present, the liquid ndll have a blue fluores- 
cence. Pure ammoniacum has a specific gravity 1-19 to 1-21, and 
the extracted resin has an acid number 69 to 80, and ester number 
19 to 38. 

The essential oil of ammoniacum has a specific gravity 0-885 
to 0-895 ; optical rotation, -j- 1° to 4° ; refractive index, 1-4720 
to 1-4810 ; and ester value about 40. It contains linalyl acetate, 
citronellyl acetate, a dihydro-sesquiterpene termed ferulene, and 
a ketone termed doremone. 

AMOMIS JAMAICENSIS. — This plant is the wild pepper 
of Jamaica. It jdelds an essential oil consisting largely of linalol. 
Its specific gravity is about 0-890. Attempts are being made to 
develop the cultivation of the plant. According to the Bulletin 
of the Imperial Institute, 1919, 3, 301, the foUovdng are the 
characteristics of the oil : — 

Specific gravity at 16° . 

. 0-8895 

Optical rotation at 22° 

. —6° 0' 

Acid value .... 


Saponification value ' . 


)j ,, after acetylation 

. 129-4 

Percentage of esters . . , 

1-5 per cent. 

„ total alcohols CjoHjgO 

. 39-4 „ 

It is soluble at 15° in 2-5 volumes of 70 

per cent, alcohol : the 

solution becomes cloudy on the addition of 6 volumes of the same 


P El^F V ilf E BY 

AMYL ACETATE.— This ester, CH;,.C 00 .G 5 Hjj, is used 
more as a flavour tlian a perfuiuc, althougli, judiciously used, it 
is very useful in the blending of fruity odours. It is the basis of 
artificial oil of jiear, and is j)reparcd by the esterification of amyl 
alcohol by acetic acid. Although usually' Icnovn as amyl acetate, 
it is actually mainly composed of i'-o-amyl acetate. It has a 
specific gravity 0-87G and boils at 138° to M0°. 

Ah'IYL ALCOHOL. — The amyl alcohol found naturally in 
Bourbon geranium and in certain euc.dyptus oils is iso-amyl 
alcohol, or isobutyl-carbinol (Cir^)XTI(Crro).(CTL,OH). It is a 
liquid, boiling at 131°, of specific gravity "o-Sl 35, and forms a 
phcnyl-urd.lianc melting at 52° to 53°.‘ This alcohol is the 
principal ingredient of the amyl alcohol produced by fermenta- 
tion, but this is usually a mixture with its isomers, so that the 
commercial esters are rarely absolutely pure chemical individu.als, 
as they are manufactured from the fermentation pj-oduct. ii'or 
the characters of the esters of pure tertiary amyl alcohol (CPbjja.C. 
CILOH, see KondakofT {.Jovr. Prahi. Chau.,' 2, 48, 4G7.) The 
commercial alcohol has a specific gravity about 0-815 ; refractive 
index, 1-4090 ; and boiling point, 130°.'^ 

AMYL BENZOATE.— This ester, CJ-r..COO.C.njp is pre- 
pared by condensing amyl alcohol and benzoic acid by means of 
liydrochloric acid gas. It is n poverful fixative, and has a slight 
“ amber ” odour. It has a specific gravity 0-094 to 1-003 ; boiling 
point, 201° ; and refractive index, 1-4045. 

AMYL BUTYRATE, Csirii.OOC.CCILJyCILj. is an ester of 
very fruity odour, used in the manufacture of fruit essences, and 
to a certain extent in the compounding of floral essences. The 
commercial article is a mixture of several isomers, of which the 
principal is iso-amyl butyrate. Its specific gravity is 0-8GG ; 
boiling point, from 109° to 180° ; and refractive index, -1-4100. 

AMYL CAPROATE. — ^This ester, also known as amyl 
hexoate, is occasionally used on account of its fruity odour. It 
is a mixture of isomers in which iso-amyl capi-onte predominates. 
It is a liquid of specific gravity 0-SG4 to 0-867, and refractive 
index 1-4210. 

AMYL CAPYLATE. — This ester (ani}”! octoatc) is very 
similar in character to amjd caproate. It is a liquid of specific 
gravity 0-8G3, and refractive index 1-4265. It consists mainly of 
the iso-anyyl ester. 



AMYL FORMATE. — ^TMs ester has a sharp fruity odour. 
It consists mainly of the iso-amyl ester, and has a specific gravity 
about Q-S80 and boils at' 120° to 125°. 

AMYL-HEPTINE-CARBONATE.— This body is one of a 
series of esters 'which have a pecuhar, fragrant odour, and which 
form the basic material in the perfumes known commercially as 
“ vert de violetle.” Theh’ preparation is due to Moureu (French 
patent 306619 of 1900, American patents 749800 and 750213). 

Heptine is an acetylenic hydrocarbon of the formula CH 3 .CH 2 . 
CH 2 .CH 2 .CH 2 .C • CH, It is prepared by various methods, such as 
from oenanthol (heptanal), a product of the diy distillation of 
castor oil. This is converted into a dichloro derivative by PCls ; 
2 molecules of HCl are 'withdrawn successively by aqueous 
and by dry caustic soda, leaving heptine. [Vide “ Heptine 

Heptine is transformed into heptin-earbonic acid by treatment 
with magnesium ethyl bromide and passing a current of carbonic 
acid gas tlirough the mixture. The heptine-carbomc acid is 
hberated from the magnesium salt thus formed by dilute sulphuric 
acid. It has the formula CH 3 .CH 2 .CH 2 .CH 2 .CH 2 .C ;• C.COOH. 
It is a hqidd of specific gra'vity 0-969. It is converted into its 
esters by warming 'ndth the corresponding alcohol and a small 
quantity of strong sulphmic acid. Amyl-heptine-carbonate boils 
at 147° to 150° at 20 mm. pressure. The methyl ether boils at 
105° to 109° at 20 mm., the ethyl ether at 114° to 117° at 18 mm., 
and the benzyl ether at 184° to 190° at 18 mm. 

AMYL HEPTYLATE. — ^This is a fairly new and very expen- 
sive synthetic perfume. Its formula is CH 3 {CH 2 ) 5 .COOC 5 Hii. It 
is an oil 'with a very powerful fruity odom’, and must be used in 
very small quantities, as other-wise its odour will spoil the prepara- 
tion it is intended to improve. Its purity may be controlled by 
saponifjdng and examiniug the resulting fatty acid, which should 
melt at — 10° and boil at 223°. 

AMYL PHENYLAGETATE.— This ester has a sweet floral 
and fruity odour. Its speciflc gravity is about 0-980 ; refractive 
index, 1-4845 ; and boiling point about 265°. It consists mainly 
of the iso-amyl ester. / 

AMYL PROPIONATE. — ^This ester resembles the acetate 
in general characters. It consists mostly of the iso-amyl ester, and 
has a specific gravity 0-873 and boils at 150° to 163°. 

47 ^ 


AMYL SALICYLATE. — This is an exceedingly popular 
S3nitlietic perfume. It is used to a considerable extent in the 
preparation of perfumes of tlie orchid, clover, and carnation t 5 ''pes. 
It is sold under such names as “ artificial orchid,” “orchidee,” or 
“ trefie.” The experienced perfumer will prefer to buy a pure 
amjd sahcylatc and dilute or blend it to his o-wn taste. 

It is prejjared by the esterification of amyl alcohol by salicylic 
acid, using sulphuric acid as the condensing reagent. It is a 
colourless oil of delightfiil odour, having a specific gravity 1*055 ; 
refractive index, 1*5050 ; and boiling pomt, 278°. 

AMYL VALERIANATE.— TJiis ester, C^Hg.COO.CsHjj, is 
IJreparcd in a similar manner to that used for the other am 5 d 
esters. It has a powerful apple odour, and is only used in small 
quantity in the preparation of fruity odours. It boils at 188° and 
is actualty the iso-valerianate, or consists mainly’ of this variety. 
Its specific gravity is about 0-8G4, and refractive index 1*4120. 

origin of the so-called West Indian sandalwood oil was quite 
unknown until Holmes, Kirkby, and Petersen {Pharm. Jonr., 
1886, iii., 16, 757, 821, 1065) decided that the plant from which 
it was distilled could not be considered as belonging to the natm'al 
order Sanialacecc. At the suggestion of E. ]\I. Hohnes, Sclninmel 
cfc Co. obtained flowering branches of the tree from Venezuela, 
and an examination of these led Holmes to the conclusion that 
the plant belonged to the natural order Ruiacece. He assumed 
it to be an unknovTi species, and named it ScMmmelia oleifera. 
It is now agreed, hoAvever, that it belongs to the species Anujris, 
and the tree is now loiown as Amyris halsamifera. The wood of 
this tree jdelds from 1*5 to 3*5 of essential oil on distillation. It 
is a viscid od of heavy aromatic odoim, resembling to some extent 
that of the true sandalwood oil. Its characters are as follows : — 

Specific gravity . . . 0*950-0*072 

Optical rotation . . . + 19° to -f- 30° 

Refractive index . . . 1*5080-1*5145 

Acid value .... 1-3 

Ester value .... 1-6 

Ester value after acetylation . 66-125 

The oil contains from 27 to 55 per cent, of a mixtm-e of alcohols 
of the formula CjsHooO. This mixture was believed by Von 
Soden [Pharm. Zeii., 1900, 45, 229) to be a single compound, and 
was by him named amyrol. Von Soden and Rojahn [Pharm. 
Zeit., 1900, 45, 878), however, then found that it was a mixture 



from ■which at least two alcohols could be isolated. These were 
found to have the follovdng characters : — 

Formula . , . O15H20O . . C15H24O 

Specific gra-vitj’- . . About 0-9S7 . . — 

Optical rotation . ’ . 36° . . 0° 

Boiling point . . 299° . . Below 299° 

The oil also contains a body of the formula O14H12O3, melting 
at 117°, which has been named amyroUn ; (Zca;fro-cadinene, and 

The oil is used in the cheaper tj'pes of perfumed soap, etc., 
where an odom resembling that of sandalwood oil is desired. 

AMYROL. — ^Amyrol is probably not an indi'sddual chemical 
compound, but a mixture of alcohols which form the principal 
odour bearer of the so-called West Indian sandalwood oil. This 
oil is distilled from the wood of Amyris halsamifera {vide “ Sandal- 
wood OH.”). The mixtui’e of alcohols has the foUo'wing characters : 
specific gravity, 0-980 to 0-982 ; optical rotation, 27° ; and 
boiling point, 299° to 301° at 748 mm. Van Sodan and Rojahn 
{Pharm. Zeit., 1900, 45, 229) claim to have separated this mixture 
into two isomeric alcohols, ha'ping either the formula C15H24O or 
^15^200 the follo'unng characters : — 

Formula .... CisHagO . . C15H24O 

Specific gravity . . . 0-987 ^ . — 

Optical rotation . . . 4-36° . . 0° 

Boiling point . . . 299° . , Below 299°. 

ANDROL. — ^This body is an alcohol, isomeric ■with citroneUol, 
found in oil of water fennel. 

ANDROPOGON IWARANGUSA. — ^This essential oil has 
been investigated by J. L. Simonsen {Jour. CJiem. Soc., 1921, 
1644). It is of interest in that it was fo^und to contain about 
80 per cent, of piperitone, the ketone discovered by Smith in 
certain eucalyptus oils (see “ Piperitone ”). The grass occurs in 
the Himalayas and outer hill zone from Kashmir to Assam, 
ascending to 8,000 feet and above, and in the plains from north- 
west Himalaya to Bombay Presidency. The piperitone present 
is dextrorotatory. 

ANDROPOGON OILS. — ^The principal oils distilled from 
plants of the natural order Grwniineoe belong to the family formerly 
kno^wn as Andropogon. Much confusion had crept into the nomen- 
clature of these plants, but it has been dissipated by Dr. Otto 
r. 40 



Stapf {Kew Bulletin, 1908, 8, 297), who has rearranged the 
classification, with general approval and acceptance. (See under 
“ Grass Oils (Perfumed) of India and Cejdon,” “ Cymbogon,” 
“ Lemongrass,” “ Citronella,” “ Vetivert,” “ Palmarosa,” etc.) 

ANETHOL. — ^Anethol CjQHjgO (iso-estragol, Methyl-pam- 
oxypropenyl-benzene) is the principal constituent of aniseed and 
star aniseed oil, and is also present to a large extent in oil of 
fennel. It is a crystalhne body, melting,at 22° to 23°, of specific 
gravity 0-985 at 25° ; refractive index, 1-5600 at 25° ; and boiling 
point, 234°. It is used to a hmited extent in perfumery, but is 
of most importance in the' preparation of anisic aldehyde, a body 
generally known as aubepine {g.v.), the basic material for the 
preparation of the hawthorn type of perfume. 

ANGELICA OIL. — ^AU parts of the Umbelliferous plant 
Angelica officinalis {Angelica Arcliangelica) yield essential oils. 
The principal of these is that obtained from the fresh root. The 
plant is found in Lapland, Sweden, Norway, Germany, etc., and 
is cultivated to a considerable extent in Saxony. The oil is used 
in the flavouring of hqueurs, etc., and to a small extent in per- 
fumery. It usually has a specific gravity 0-855 to 0-920 ; optical 
rotation, -f- 16° to + 40° ; refractive index, 1-4770 to 1-4880 ; 
and ester value, 12 to 40. Roure-Berlrand Fils {Bulletin, October, 
1921, 34) have distilled an oil from the fresh roots which had a 
specific gravity 0-8907 ; optical rotation -t- 6° 42' ; and ester 
number, 45. The flavouring constituents are not well understood. 
Japanese angelica oil is obtained from Angelica anomala, and has 
a shght odour of musk. 

ANISEED. — Two entirely different plants, belonging to dif- 
ferent natural orders, yield aniseed oils which are practically 
identical. The true aniseed ofl. is obtained from the fruits of 
Pimpinella Anisum (N.O. Umhelliferce). The so-called star 
aniseed oil, which forms the bullc of the world’s supply, is the 
product of the fruit of Illicium verum (N.O. Magnoliacece). Except 
for the fact that the oil from the true aniseed is rather more dehcate 
in odour, the two oils may be regarded as identical. They are used 
for flavouring to a considerable extent, and to a small extent in 
perfumery. The chief value, however, of aniseed oil to the 
perfumery industry lies in the fact that it provides the raw material 
for the manufacture of aubepine. 

The star anise {Badiane) is chiefly found in southern China and 
Tonkin. The oil is distilled, principally by natives, and sold to 



mercliants, wlio transfer it to Hong Kong, where it is bought bj’’ 
exporters and sent thence to Europe and America. Adulteration 
Avas at one time very extensive^ practised, chiefly by a group of 
Chinese merchants who were known as the Bande Noir, but 
to-dav the oil reaches Europe in a state of purity, and is seldom 
ji(Jutterated. The process of distillation is as follows. About 
20 lb. of the fruit are placed in an iron pan and covered with 
water. A second iron pan is placed upon tliis, upside down, so as 
to form a cover. The latter vessel is pierced with a circular 
opening, over wliich is placed an earthen vessel with three small 
orifices in the lower part, which allow the access of vapour. These 
orifices are- covered on the inside by small ear-shaped hoods, 
which cause the vapour to be spread over the sides of the vessel. 
This earthen vessel is covered with an iron pan, which acts as a 
refrigerator and into which a continuous current of cold water is 
admitted. The joints of the first two iron pans are luted, and the 
earthen vessel and refrigerator are jointed -uith cloth bandages. 
The vapour reaches the earthen vessel and is condensed when it 
impinges against the refrigerator, and falls into a circular trough 
at the bottom of the vessel, whence it escapes through a small 
pipe. The annual exportation of star aniseed oil varies from 
60,000 to 200,000 kg. per annum. 

Illickm verum is a small tree, growing to the height of from 
8 to 15 metres. The trunk, which is frequently bifurcated at the 
base, is from 25 to 30 cm, thick, and rises to a height of 1-5 to 
2 metres -without brandling. The leaves are evergreen, the flowers 
appear twice a j’ear, and the young fruits are star shaped, w’^hich 
gives the name to the tree. The yield of oil varies from 2-5 -fco 

5 per cent. The essential oil is, at ordinary temperatures, a solid 
crystalline mass having the foUowing characters : specific gravity 
at 20°, 0-980 to 0-990 ; optical rotation, + 1° to — 2° ; refractive 
index, 1-5530 to 1-5565; melting point, 16° to 19° ; congealing 
point, 15° to 17-5°. 

The true aniseed, Piinpinella Anisnm, is found in many parts of 
Europe, principally, however, in Russia. According to ScJdmmel 

6 Co., the following yields are obtained from the fruit as gro-wui in 

various countries : — 


1-9 to 2-6 


Per cent. 

2-7 to 3-5 




2-4 to 3-2 

Mexico . 

1-9 to 2-1 

East Prussia . 


Russia . 

2-4 to 3-2 

Spain . 



1-5 to 6-0 



61 1-2 


In Russia anise is grown in the county of Voronetz in the 
districts of Biriutch, Ostrogojsk, and Valuild, and the oil is, as 
mentioned above, practically identical with star anise oil. 

The following bodies have been identified in star aniseed oil : 
f?e.rfo'o-pinene, phellandrene, cymene, cineol, dipentene, limonene, 
terpineol, methjd-chavicol, liydrokmone-ethyl-ether, safrol, a 
sesquiterpene, anise ketone, and anethol. True aniseed oil has 
not been so exhaustively investigated, and the only bodies so far 
detected are anethol, methyl-chavicol, anise-ketone, and aldehyde. 

The fruit of a plant Seseli HaTveyanum, known in Victoria 
(Australia) as aniseed (but which more closely resembles fennel), 
has been examined by XJmney and found to contain anethol, but 
in considerably less quantity than ordinary aniseed oil. There is 
also a false aniseed, IlUcium religiosum, known in Japan as 
SMlcimi-no-M. It contains eugenol, cineol, safrol, and a mixture 
of terpenes. The principal adulterant of aniseed oil is petroleum 
oil. The pm’e oil is soluble in 3 volumes of 90 per cent, alcohol, a 
feature which is interfered vdth by the presence of petroleum. So 
long as the congealing and melting points of the oil fall within the 
limits given above, it is most unlilccly that the oil is adulterated. 
It must be remembered, however, that aniseed ofi. is one of those 
oils with a considerable tendency to remain in a state of super- 
fusion, so that it may be cooled dovm to well below its congealing 
pouit vnthout becoming sohd. To determine these temperatines, 
a small quantity of the oil should be placed in a narrow test-tube 
and cooled down to about 10°. If it does not congeal on stirring 
with a small-bulbed thermometer, a crystal of anethol should be 
added, when the mass will rapidly crystallise. It should be gentty 
stirred, and the temperature rises as crystallisation takes place. 
The maximum temperatme is noted, and is taken as the con- 
gealing point. The tube is then gently warmed by holding in the 
hand, and the contents kept stirred all the white by the ther- 
mometer. The temperatm’e at which the crj^stals completely 
disappear is taken as the melting point. Oils with congealing 
points of 12° to 13°, but which are soluble in 90 per cent, alcohol, 
are not lilcely to be adulterated with petroleum, but may be 
adulterated with a fraction of camphor oil, or by tlie abstraction 
of anethol. An oil adulterated in this manner has been examined 
by E. J. Parry {Chemist and Druggist^ 1910, 687). Its characters, 
compared mth those of a pure oil, were as follows : — 

Adulterated. Pure. 

Specific gra\fity at 20° . 0-972 . . 0-982 

Optical rotation . . 0° .. — 1° 10' 

62 ■ . 


Refractive index at 20° 



Pure. - 


Melting point . * . 



Congeahng point 



Refractive index of first 10 per 
cent, distilled 



Refractive index of last 20 
per cent. 

1-540 ‘ 


has been found as a constituent of Tahiti vanilla beans. It is 
produced artificially b}'^ the action of caustic potash on anisic 
aldehyde. It forms colourless crystals melting at 45°, and boiling 
at 259°. It forms a phenjd-urethane melting at 93°. 

ANISIC ALDEHYDE. — ^This ai'tificial jrerfume is laio\m 
commercially as aubepiiie, or artificial hawthorn. It is a methyl 
ether of para-ox 3 '--benzaldehyde, of the formula CgHgOo. It is an 
oil having the following characters: specific gravity, 1-1275; 
optical rotation, 0° ; refractive index, 1-5730 ; and bo ilin g 
point 246°. 

Anisic aldehyde is the basic material for all perfumes of the 
“ may blossom ” type. 

A small amount is obtained as a by-product in the manufacture 
of coumarin, but it is usually manufactured on a commercial scale 
by the following process. Star aniseed oil is warmed for an hour 
or two with three times its volume of nitric acid (specific 
gravity, 1-1), and the heavy oil separating is washed vdth potash 
solution. This oil is crude anisic aldehyde. It is combined with 
sodium bisulphite' by shaking it with a hot solution of that salt, 
and the resulting crystals are washed with alcohol, dried on porous 
paper, and dissolved in water. It is then warmed with solution 
of sodium carbonate, and the resulting anisic aldehyde is separated 
and rectified. 

Aubepine is also manufactured commercially by treating toluene 
sulphonic chloride, a by-product in saccharine manufacture, with 
a solution of soda ash at 100°. The p-toluene sidphonate of 
sodium resulting is melted with caustic potash, and the resulting 
para-cresol hberated by hydrochlorie acid ; this is then esterified 
with dimethyl sulphate, and the resulting para-cresol methjd ether 
is dhectly oxidised to anisic aldehyde. 

The solid aubepine of commerce is the combination of the 
aldehyde with sodium bisulphite, but is now seldom employed. 

ANISYL METHYL KETONE. — See “ Methoxy-aceto- 




ANTHRANILIG ACID ESTERS.— AiitliraiiUic acid, or 
ortho-amido-benzoic acid C^H^’NHo'COOH is one "which forms 
several higlily odorous esters, of which the most important 
naturally occurring compound is methyl anthranilate CfjH.j.NHo 
COOCH3. The only other ester of an}’" particular importance is 
ethyl anthranilate. Meth 5 d-anthranilic acid also yields similar 
esters, of which the methyl ester occurs naturally. 

Methjd antliranilate is found m the essential oils of neroli 
petitgrain, jasmin, gardenia, and tuberose, frecpiently associated 
vith methyl methyl-anthranilatc. 

Anthranilic acid is manufactured on a commercial scale by 
first oxidising naphthalene by means of fuming sulphuric acid in 
the presence of salts of mercury. Forty grams of mercury are 
dissolved in 1 kg. of sulphuric acid, and the mixture is heated until 
the sulphuric acid distils. To this is gradually added a mixtmre, 
prepared three hom's previously, of naphthalene 3-5 kg., suljphuric 
acid (66°. B.) 37 kg., and fuming sulphuric acid 10-5 kg. The 
phthahe anliydride formed distils over with some sulphuric acid, 
from which it is freed by washing. It is finally subhmed, when 
it should melt at 128°. 

Phthahe acid is melted and brought to a temperature of 140°. 
A current of dry ammonia gas is then passed through it, the 
reaction temperature being gradually increased to 240°. This 
results in the formation of phthahmide CgH.i(CO) 2 NIi. Phthali- 
mide is treated "with potassium h 5 'pobromite or hypochlorite in 
the presence of excess of aUvah, and anthranihe acid results. On 
recrystalhsation the pure acid melts at 144° to 14-5°. There are 
several other methods by which this acid can be obtained, but the 
above is the most practical. The acid is esterified with methyl 
or ethyl alcohol, as the case may be, using hydrochloric acid as the 
condensing agent. 

Methyl anthranilate CgH^lNHalCOO.CHg is a crj^stalline body 
melting at 24°, and boiling at 135° at 15 mm. Its specific gravity 
is 1T68. Eth}^ anthranilate is a hquid boiling at 145° at 20 mm. 
Both esters have a characteristic neroli odour, that of the ethyl 
ester being sweeter and softer. 

If methyl antliranilate be heated with methyl iodide and water 
for several hours under a reflux condenser, methyl methyl- 
antliranilate, melting at 18°, results. 

F. B. Power {Jour. Amer. Ghcm. Soc., 1921, 43, 377) has 
published a method for the detection of methyl anthranilate in 
fruit juice, in which 500 c.c. of the juice are steam distilled 



tmtil 200 c.c. have come over, when, if appreciable quantities of 
methj^l anthranilate are present, the solution -will show a bluish 
fluorescence. At this stage the ester is extracted from the distillate 
by three successive quantities of clfloroform of 10 c.c. each. The 
chloroform extracts are filtered, and the solutions evaporated on 
the water hath. Two cubic centimetres of 10 per cent, sulphuric 
acid solution are added to the residue, and the mixture is trans- 
fen-ed to a test-tube. During the evaporation of the chloroform 
extracts, etc., there is prepared a mixture of 1 c.c. of 0-5 per cent, 
pm-e beta-naphthol solution, 1 c.c. of 10 per cent, solution of 
sodium carbonate monohydrate NaoCOg-HoO, and 1 c.c. of a 
10 per cent, solution of caustic soda. On adding the ester solution 
in the test-tube to this mixture, the presence of OT mg. or more 
of the methyl anthranilato will be shown by the formation of 
yeUowish-red coloration. 

Another method is to add a drop of dimethylanihne to the ester 
solution, and, when solution results, the addition of a slight excess 
of caustic soda will give a yellow coloration, which is changed to 
red by the addition of a little dilute acid. 

The quantitative determination of methyl anthranilate is best 
carried out by the method suggested by Hesse and Zeitschel. 
Trom 25 to 30 grams of the sample are dissolved in two to three 
times its volume of- perfectly dry ether. The mixtime is then 
cooled in a freezing mixture, and then a mixtiue of 1 volume of 
sulphuric acid and 5 volumes of ether is added slowly until no 
further precipitation takes place. The whole of the methyl 
anthranilate is thus precipitated as sulphate. The precipitate is 
collected, washed vuth ether and weighed. This gives the 
approximate amount of' the ester present. For a more exact 
result, the precipitate may be titrated vdth semi-normal potash 
solution. If P be the weight of oil employed and N be the number 
of cubic centimetres of semi-normal allrali used, then the 
percentage of methyl anthranilate is given by the formula 

r 3-775 X k 

P A. G. 

AQUILARIA GRAS SNA. — ^This plant, growing principally 
in Cambodia, is liable to be infected with a disease, the nature of 
which is not yet understood, which, causes the wood to become 
resmous and highly odorous, especially when burned. The wood 
is used in the preparation of Chinese joss sticks, and for incense 
purposes generally. (Vide La Parfumei'ie Moierm, 1923, 124.) 



ARMENIAN PAPER. — ^The so-called Armenian paper is an 
absorbent paper saturated with an aromatic solution and dried 
so that, when burned, it evolves an odour of the type of incense. 
The paper is made by making an, alcohohc solution of the following 

Frankincense- . . . .2 parts. 

Storax ...... 2 ,, 

Gum benzoin . . . . 2 ,, 

Balsam of Peru .... 0-5 part. 

Balsam of tolu .... 0-5 ,, 

90 per cent, alcohol . . .5 parts. 

To this is added sufficient of a saturated solution of potassium 
nitrate in water to enable the paper to burn freely, and the 
absorbent paper is then soaked in the mixtrue, drained, allowed 
to dry in the air, and cut into convenient stri^DS. 

AROMADENDRAL. — ^This body is an aldehyde of the 
formula CgHigO, isolated by Baker and Smith from various oils 
of euealyptus. It has a pleasant odour, resembling that of 
cumie aldeh3ffie, with -which Schimmel & Co. consider it to be 
identical. It has a specific gravity about 0-950 and boils at about 

ARTEMISIA OILS. — Certain of the oils distilled from 
species of Artemisia (N.O. Compositoe) are used to a considerable 
extent in flavouring, and to a small extent in perfumery. The 
principal of these is the oil of Artemisia Absinthium, oil of worm- 
wood or oil of absinthe. The plant is indigenous in the Old World 
as far north as Scandmavia, Finland, and Siberia, and appears 
to have migrated to North America, It is found wild in some 
parts of Great Britain, and is eultivated in the United States, 
Russia, Algeria, Corsica, Spain, and Italy. The principal areas 
under eultivation in the United States are situated in Wayne 
County and in Sauk Count}^. 

The eharaeters of the oil vary considerably, according to 
vffiether the herb is fresh or dry or in an intermediate condi- 

It is a somewhat viscid liquid, usually of a dark green or blue 
colour, but sometimes dark brown. The colour appears to be 
dependent on the length of time taken by the distillation. 

Gildemeister and Hoffmann (2nd Enghsh ed,, vol, 3, p. 640) 
give the follovdng figures for genuine samples of the oil as found 
in commerce : — 








Spe ific^praYity, 

0-901— 0-954 




Eefractive index 



Acid value 

Up to 6-7 

Up to 6-1 

Up to 5-6 

Up to 2-2 

Ester value 

Ester value after 

11 to 108 

14 to 93 

15 to 37 

46 to 89 

acetylation , 





Schimmel & Co. distilled a number of specimens of the herb 
grown at IMUtitz and at Barreme, and give the following results 
for the oOs obtained ; — 


Yariety of Herb, 



French grown in 

Specific gra-vity 

Acid value 

Ester value . 

Ester value after 





0 - 2 - 8-6 



Up to 1-5 



Variety of Herb, 



Specific gravity 

Acid value .... 

Ester value .... 

Ester value after acetylation 

Up to 3-2 

0 - 936 - 0-939 
Up to 2-8 
96 - 4 r -114 

An oil distilled from wild Dalmatian herb had a specific gravity 
0’9188.; acid value, 1*3 ; and ester value, 64-6 [Schimmel t& Co., 
Report, October, 1911, 101). 

E. R. Miller [Bulletin Univ. Wisconsin, 693) has examined six 
samples of Wisconsin oils, and found them to contain from 25-8 
to 35' 1 per cent, of esters calculated as thujyl acetate, and from 
8-9 to 21*6 per cent, of free alcohols as thujyl alcohol. 

Charabot [Comptes Renclus, 1900; 130, 923) has shown that 
the proportion of thujone to thujyl alcohol in the oil changes as 
the plant develops, the thujone being graduallj'^ converted into 
thujyl alcohol. 



Boure-Berirand Fils {Bulletin, April, 1906, 36) give' the follow- 
ing results from two oils distilled from wild plants grown in the 
hills round about Caussols (Alpes Maritimes) : — 

Esters . 


Per cent. 


Per cent. 



Combined alcohols . 

. 7-0 


Free alcohols . 

. 71-9 





The oil contains, in addition to thujyl alcohol and its esters, 
thujone, phellandrene, cadinene, traces of pinene, and a blue 
compound known as azulene. The thujone present exists in two 
isomeric modifications. 

Artemisia arborescens is a shrub-like plant common to the 
Mediterranean countries. Scliimmel & Co. [Report, November, 
1908, 136) have examined a sample of the oil which had a deep 
blue colour. Its specific gravity was 0-9458 ; acid value, 9-8 ; 
and ester value, 19-5. Jona [Ann. Chim. Appdie., 1914, 1, ii., 63) 
found 14 per cent, of alcohols present, including thuj3d alcohol 
and bonieol, and 13 per cent, of thujone. 

Pellim and Morini [Biv. lial, del Essences et del Prof., December, 
1923) give the foUovdng characters for this oil : — 

■ ■ . _ — - - . . .. 1 






Specific gravity 




Acid number . 




Ester number . 




Ester number after acetylation . 




Ester per cent. 




Free alcohols per cent. 



Total alcohols per cent. 




Yield per cent. 





Artemisia vidgaris is a common weed, which grows along 
hedges and road sides, and wliich yields about 0-1 per cent, of 
essential oil of specific gravity 0-907. It contains cineoL It 
appears, however, that this oU Offers greatly in character, accord- 
ing to its place of origin. Two samples, known as yomugi oil 
in Japan, which were probably derived from A. vulgaris, were 
examined by Scliimmel cb Go. [Report, October, 1903, 78 ; April, 
1904, 78), and found to have the following characters : — 

Specific gravity . 0-910 . . 0-9126 

Optical rotation . —13° 16'" .. — 18° 50' 

68 " 


: ttr j-f®’ 

Ester value . . 29-8 

examined at the Imperial Institute under the name 

tion value 108-q- -a 0-939 ; sapomfica- 

2 . 

- - 0-949 (at 20°) 

Specific gravity 
Optical rotation 
Eefractive index 
Acid value . . 

Ester value 
Ester value after 

— 8° 52' 

+ 57° 2' 


- ' ' 55-5 ^ ^ 228 

(See also ScUmmeVs Report, Koyembor, 190S, 140.) 


Artemisia (?fefe‘?i05a.— Bennett (P. & E O T{ loon - oo,.^ 
lias examined the essential oil dist lied from SSs 2/"’ i 

Specific gravity 
Optical rotation 
Refractive index 
Total alcohols as borneol 
Esters as bornyl acetate 
Phenols . . , ' ' 

. Aldehydes and ketones , jg 

- Eor other artemisia oils, see E J Parrv " Ti <a r<u ” • jl 
Essential Oils, etc.” (4th ed., vol 2 p 29^’ 7 Chemistry of 

Oil/’ » Gougt, Oil of,” and » Scinch, Oil of!” 

artificial esters in ESSPKrTTAT r^rr ^ 

artificially prepared and are '5’'’°'* *° ““ 

to raiee esr/aCofX ofl ” “ -^er 

0- 937 
+ 24° 

1- 4780 

17-5 percent, 
6-3 „ 





As it has become the custom to value certain essential oils, 
such as lavender, bergamot, etc., b}^ their ester content, the 
detection of the addition of these artificial esters is of importance. 

The prmcipal esters used for this piu’pose are terpinyl acetate, 
gtyceryl acetate, ethyl citrate, ethyl succinate, ethyl tartrate, 
ethyl phthalate and ethyl laurinate. 

Them boiling jDoints and sjDecilic gravity are as follows : — 

Acetine . 
Ethyl citrate 
Ethjd succinate 
Ethyl tartrate . 
Eth 3 d phthalate 
Eth 3 d laurinate. 

Boiling point. 

261°-264° C. 
2G0°-265° C. 
258°-260° C. 
28G°-289° C. 
212°-218° C. 
278°-282° C. 
290°-293° C. 
270°-310° C. 

bpeciuc gravity 
at 15 -5° C; 


the detection 

It is impossible to outlme a general method for 
of artificial esters, but, as a rule, tlie 3 ’' can be partially separated 
by fractional distillation, and then b37' comparmg the ph 3 '-sical 
characters of the last fractions with those obtained from oils of 
knovui purit 3 '’, indication of the presence of abnormal con- 
stituents may usually be obtained. 

B 3 '’ saponifying the high-boiling ester-containing portion with 
alcoliolic potash, neutralising vdth acetic acid, evaporating the 
alcohol, and extracting the oily matter by shaking with ether, 
abnormal potassium salts may be detected in the aqueous portion 
by evaporating to di’3mess, dissolving in water, and applying the 
usual chemical reagents, such as barium chloride, calcium chloride, 
ferric chloride, etc. 

As a test for the presence of esters of non-volatile acids, such 
as citric, tartaric, succinic, and particularly plithalic acid, the 
test devised by Bennett (P. cb E. 0. R., 1923, p. 359) is extremely 
useful. Tills test is carried out as foUows : — 

One cubic centimetre of the oil for examination is placed with 
3 c.c. of an approximately 10 per cent, solution of caustic potash 
in dbsohite alcohol in a test tube, the whole immersed in a water 
bath for a few minutes, and then allowed to cool. If no precipitate 
forms ivithin one hour at the most, the oil may be considered 
unadulterated with these esters. 

Another method by which the presence of non-volatile acids 
can be detected has been devised by Messrs. Schimmel {ScliininieV s 
Bericht, October, 1910, p. 43 ; April, 1911, p. 151). 



This test depends on tlie fact that the esters natural present 
in essential oils are esters of volatile acids ; if the ester number 
of the oil be determined in the ordinary way, and the mixture 
then made acid and steam distilled, the distillate should require 
almost the same amount of standard allmli for neutralisation 
as was absorbed in determining the direct ester value ; a difference 
of more than 10 in ester number between the two titrations 
indicates the presence of esters of fixed acids. 

This method has been the subject of various criticisms (P. cC* 
E.O.R., 1914, p. IIG; 1923, p. 293; iSchimmcl's BerkJif, 1924, 
p. 123) and modifications, but it is nevertheless an extremely 
useful one. It is, however, likely to give inconclusive results 
uhen lauric esters are present, as these are somewhat volatile in 
steamJP. * E. 0. R., 1919, p. 17e ; Schimmers BericJil, 1924, 
p. 125), and thej’ are best detected bj"" a special method, which 
will be described later. 

Ghjccnjl Acclate. — ^This adulterant is usually a mixture of 
glycciyl acetate in which triacctine predominates. 

Its detection is comparatively’- easy, as it is soluble in warm 
water, and also in 5 per cent, alcohol solutions. 

Messrs. Scliimmcl {SchimmeVs Report, October, 1910, p. 61 ; 
April, 1911, p. 150) have iH’oposcd the folloufing method for its 
detection : — 

Ten cubic centimetres of oil and 20 c.c. of 5 per cent, alcohol 
are well shaken in a separating funnel, and after the solutions 
have separated and become clear, the watery solution is run off 
and filtered. Ten cubic centimetres of the filtrate are exactly 
neutialised -uith decinormal allcali, and 5 c.c. of semi-normal 
allcali run in, and the whole saponified undei* a reflux condenser 
for one houi’. In the case of a pure oil, O-l or, at most, 0-2 c.c. 
of semi-normal alkali will have been used up by the saponification, 
w'hilst each 1 per cent, of glyceryl triacetate jwesent in the oil 
will be represented by practically 0'5 c.c. of semi-normal alliali. 

glyceryl acetate is so easily’- washed out with hot water, a 
simple method {P. di E. 0, R., 1912, p. 275) is to wash the oil 
several times until hot water. When the oil is adulterated, the 
washed oil unll show a distinctly lower ester value than the 
original unwashed oil, while in the case of a pure oil the ester 
value of the washed oil is practically the same as that of the 
"unwashed oil. A difference in the refractive indices of the washed 
and original oils will also be found when this adulterant is present. 

Hall and Harvey (P , tfc E, 0. R,, 1913, p. 6) determine glyceryl 



acetate in essential oils by a method in wliich the glycerol is 
separated and weighed. 

T-erpinyl A cetaie. — ^This ester is hydrolysed with . greater 
difficulty than the usual natural esters present in essential oils, 
and Messrs. Scliimmcl {ScIiimmeVs Report, October, 1910, p. 60) 
have devised a method for its detection, based on this fact. 

This method is to saponify for one hour and two hours, using 
only half the amount of semi-normal allcali for the one-hour 
saponification that is used for the two hours’ saponification. In 
the case of pure oils, the difference between one hour and the 
two hom’s’ saponification values should not amount to more 
than 3 ; if 6 per cent, of terpinyl acetate is present, a difference 
of as mirch as 14 is sometimes found. 

Laurie and oilier Fatty Esters. — ^These esters give no precipitate in - 
Bennett’s test, and as some of them are somewhat volatile in steam, 
they are not easily* detected by ScliinimeVs method for detecting 
non-volatile fatty acids {SchimmeVs Bericlit, October, 1910, p. 43; 
April, 1911, p. 151, 1914, p. 125 ; P. E. 0. R., 1919, p. 175). 

In order to detect these esters, it is best to sejDarate out the 
fatty acids, and this is carried out as follows ; — 

Ten cubic centimetres of the oil are saponified for one hour 
with 20 c.c. of 2/N alcoholic potash. Twenty-five cubic centi- 
metres of viator are then added, and the bulk of the alcohol is 
evaporated off. The solution is then almost neutralised to 
phenolphthalein, and the unsaponified oil removed by shaking 
out tlu’ee times with ether. 

The aqueous solution is then made acid to methyl orange, and 
shaken out with ether. 

The ethereal solution wiU now contain acids, such as benzoic, 
cinnamic, oleic, phthahe, and lauric, and these vdll be obtained 
in a moderatel 3 ’- pure condition by evaporating off the ether. 

M. S. 

ASAFCETIDA. — ^This substance is a foul-smelling gum-resin 
which, ui an extremety diluted condition, is of value both as a 
flavour and as a perfume. It is obtamed as an exudation from 
the cortex of the stem and root of various species of Ferula, 
prmcipally F. fostida, F . scorodosma, and F. narthex. Its popular 
name is “ Devil’s dimg.” It is used in the form of a tmeture in 
70 per cent, alcohol. Its jDrincipal constituent is the feruhe ester 
of asaresinotannol. A good sample should not contain more than 
10 per cent, of ash (earthy matter), the best samples contahiing 
from 3 to 5 jDer cent. It yields an ’essential oil consisting principaUj’’ 



of all}-! sulphides, and having a specific gravity 0-915 to 0-993 ; 
optical rotation, + 10° to — 36° ; and refractive index:, 1-4940 
to 1-52G0. (Refer Unmey and Bunlcer, P. E. 0. R., 1910, 165.) 

ASARUM GANADENSE, OIL OF. — ^The rhizomes of the 
Canadian snakewood plant {Asarum canadcnse) yield 3 to 5 per 
cent, of essential oil having a specific gravity 0-950 to 0-952 ; 
optical rotation, — 2° 50' to — 10° 40' ; and refractive index, 
1-4850 to 1-4S90. It contains pinene, linalol, borneol, terpineol, 
geraniol, methjd-eugenol, fatty acids, and a lactone of unlcnown 
constitution. Its odour is pungent and aromatic, recalling 
patchouli and ginger. It is used in the United States for giving 
a special “ note ” to cau de Cologne. 

ATTAR OF ROSE.— See " Rose.” 

AURANTIENE. — ^This name is given to the terpenes of 
orange oil, produced in the manufactm-e of terpeneless orange oil. 
It consists of limonene, principally in the dextrorotatory form. 

BACKHOUSIA OILS. — BacJchousia citriodora, a small tree 
growing in Queensland, yields about 1 per cent, of an essential 
oil of pleasant verbena odour, which is used in perfumer}’’ to some 
extent, but which is now onl}’’ produced on a small scale, o^ving 
to the fact that lemongrass oU, which it closely resembles, is sold 
at a cheaper rate. The oil contains from 90 to 95 per cent, of 
citral {vide “ lonone ”). It has a specific graAity 0-895 to 0-900, 
refractive index 1-4860 to 1-4889, and is optically inactive. 

Bachhoiisia myrtifolia also jields a pleasant-smelling essential 
oil, of -wLich the principal constituent is the phenol ether elemicin. 
It has a specific gravity 1-026 to 1-057. 

BacHiousia angusiifolia jdelds an essential oil of pleasant- odour, 
w'hich contains about 60 per cent, of a body w’hich is probabty 
a phenol allied to tasmanol and leptospermol. It has been 
investigated by A. R. Penfold, of the Technological Museum, 
Sydney {Jour. Roy. Soc. N.S.W., 57, 300). A yield of 1-05 per 
cent, on the dried leaves and terminal branchlets w’as obtained. 
The oil is of particular interest, since it differs materially from 
any Baclchousia oil hitherto described, and contains about 75 per 
cent, of a hitherto undescribed - bodj’, which appears to be a 
phenol. Dextro-a-pinene, ^-pinene, cineol, a-tei’iDineol, sesqui- 
terpenes, and a solid body — probably a lactone — melting at 118° 
to 119 'W’ere also identified in the oil. The principal constituent 
is a somewhat remarkable compoimd, and appears to belong to 



the grouj) of Ijoclies of which tasmanol and leptosperinol are 
recognised constituents. Pcnfold classes it tentatively as a 
phenol. Pour oils also examined had the following characters : — 





Specific gravity 





Optical rotation 

-f 1-55° 


— 1-2° 

+ 0-6° 

Befractive index 





Acid number . 



— - 

Ether number . 




Ester number after 

acetylation . 




, ■ 

Phenols . 

75 per 

75 per 

60 per 

26 per 





After extracting the phenols with a caustic soda solution, the 
non-phenolic residues resembled eucal^yptus oil in odonr, and had 
the following characters : specific gravit}^ 0-903 to 0-90S ; optical 
rotation, + 6-1° to -|- 8-25° ; refractive index, 1-4655 to 1-46GS ; 
cineol, 30 to 50 per cent. This portion of the oil was used for 
the determination of the various constituents mentioned above. 
The stearoptene was ciystallised from alcohol, and melted at 
118° to 119°. The formula appears to be CjgHjnOg, which was 
confirmed bj'- crjmscopic determination of the molecular weight. 
The phenolic constituent is a viscous liquid, giving a brilliant 
orange colour with ferric chloride, and is slightly Icevorotatory. 
Its formula is probabty CioHj,j 03 , and its characters are given 
in the following table. Pom’ different specimens are included 
from different sources, and obviously traces of impurities are 
present in some of them, especially No. 1. 





Boiling point, 

10 mm. . 





Specific gravity . 





Optical rotation . 

— 0-55° 


— 4-65° 

— 4-45° 

Befractive index . 





Backlioiisia sciadophora jnelds an oil of specific gravity about 
0-880, and optical rotation -}- 34°. It consists in the main of 
pinene (80 -to 85 per cent.), a sesquiterpene, a sesquiterpene 
alcohol, a phenol, and caprylic acid in the form of esters. 

BALM OF GILEAD. — ^This balsam, also Imown as Mecca 
balsam, is the product oi 'Ealsamodendron GUeadensc or B. Op)o- 


P E RF U 21 E B Y 

baUaym^n, the former plant probably being a variety of the 
latter. The tree is found principally in Arabia. An interesting 
historical account of it is given by de Sacy C Relation' de 
PEgypte/*’ Paris, 1810). It '^as cultivated — and it^ is very 
difficult to cultivate — ^in a garden at Matriya, near Cairo, from 
the eleventh up to the seventeenth century, where it was so valued 
that the garden was completely walled in and was guarded by 
janisaries. Abd-ul-Latif {obit 1231) gives an account of the 
preparation of the balm. Incisions were made in the bark down 
to the wood (apparently to injure the cambium cells and induce 
a pathological secretion), and the juice exuding was scraped from 
the tree and preserved in bottles, which were buried in the earth 
for a time, and afterwards exposed to the sun until the balsam 
had separated from the impurities. It was then subjected to some 
secret process, and finally stored in the royal treasury. In lo60 
only nine or ten trees remained alive in this garden, and no balsam 
was yielded by them. The last tree perished in 1615 tlirough an 
inundation of the Nile. It now grows in Arabia, in the neighbour- 
hoods of Medina and Mecca. About the beginning of April the 
trees drop their juice from cuts made in the smaller branches. 
An inferior balsam results from boiling the twigs and skimming 
off the floating material from the water. 

The genuine balsam, which is very rarely found in commerce, 
is at first turbid and white, but thickens with age and becomes 
of a honey colour. It is adulterated with turpentine, Chian 
turpentine, Canada balsam, and common rosin. Having a low 
acid value, it does not solidify when triturated with an eighth 
part of its weight of magnesia, as do most of the pine resins. A 
reasonably fresh, pure Mecca balsam should have an acid number 
of about 40, and an ester number about 100. It is used in the 
manufacture of some Oriental perfumes. 

BALM, OIL OF.— Oil of balm, or melissa oil, is distilled 
from the herb Melissa ojjicinalis, a plant belonging to the natural 
order Labiates • It is a native of western Asia, and is fairly widely 
distributed. The name is derived from the Greek melissa^ a bee, 
and is indicative of the attraction the flowers have for bees on 
account of the saccharine matter they produce on a considerable 
scale, and which suits the bees for the secretion of honey. The 
leaves have a pleasant odour recalling lemongrass and citronella. 
The essential oil is scarcely a commercial article in the pure 
state, as the yield obtained will not allow the oil to be sold 
remuneratively. It is a liq^uid of specific gravity about 0*895 to 

p 65 , ^ 


0'925, and contains citral, citronellal, geraniol, linalol, and 
citronellol. The oil of balm of commerce is either lemon oil 
distilled over melissa leaves, vitli a little citronella oil added, or 
the melissa leaves are omitted and the oil is entirely factitious. 

BALSAMS. — ^The term “balsam” is an inexact and elastic 
one, and is incapable of scientific definition. From the point of 
view of the perfumer, the aromatic balsams may be taken to be 
oleoresinous exudations of plants, sometimes normal, sometimes 
pathological, often containing oifiy very little essential oil, but 
always containing odoriferous '^constituents, most frequently 
benzoic or cinnamic acids or their esters. Commercially the term 
is usually restricted to exudations from the plant, but scientifically 
there is no reason to distinguish between these exudations and 
aromatic oleoresins extracted from the plant by solvents. Such 
bodies are benzoin, storax, balsam of Peru, balsam of Tolu, 
labdanum, etc., all natural exudations ; and such bodies as oak 
moss or orris resin, oleoresins obtained by extraction vdth 
solvents. Most of this group of bodies — ^indeed, practically all 
of them — are of the greatest value as fixatives, subject to this 
qualification. If an oleoresinous material has a strong and 
pronounced odour, it can only be used as a fixative where its 
odour will blend with the other perfumes used, unless it be so 
' powerful a fixative that verj^ small quantities can be employed. 
Apart, however, from this characteristic of these substances, most 
of them are highly odorous, usually having a heavy odour of the 
so-called Oriental type, for which class of perfumes ■ they are 
invaluable as actual odour bearers, apart from their fixative 
value. (See also “ Fixatives.”) 

BALSAMO BLANCO. — ^This substance, Imown also as White 
balsam of Peru, is said to be obtained from the fruit pods of 
Myroxylon Pereirce. Germann, however, states that this product 
differs from the wliite balsam of Peru which he has exa min ed, and 
considers it may be identical vdth American storax from Liqui- 
damhar styraciflua. It rarely finds its way into commerce to-day. 

BALSAM OF PERU. — ^This substance is of the greatest 
value in the preparation of heavy odom’s of the Oriental type. It 
is also much valued as a fixative. It is an oleoresinous liquid, 
of the consistency of a thick syrup, obtained from the trunk of 
Myroxylon Pereirce, a leguminous tree growing in the forests of 
San Salvador, in South America. The secretion is not a natural 
one, but is pathological, being induced by the gentle heating, and 



then scorching, of the bark. As the liquid exudes it is soaked up 
by cloth, -with which the wounded places are covered. The cloths 
are pressed and boU’ed with water, and the balsamic liquid is 
separated, and is then ready for export. 

Balsam of Peru is a dark, reddish-brown liquid of great viscosity ' 
and of a penetrating and very sweet odour. It contains from 
55 to 65 per cent, of a substance known as cinnamein, which, 
however, is not a definite chemical individual, but is a mixtm’e of 
esters of both cinnamic and benzoic acids. It also contains a 
small amount of free aromatic acids and alcohols, and a trace of 
va nillin . The alcohols combined vdth the aromatic acids are 
principally benzyl alcohol and peruviol. 

When pure the balsam has a specific gravity 1'1400 to 1-612, 
refractive index 1-5800 to 1-5855, and contains from 50 to 65 per 
cent, of cinnamein, which can be estimated in the following 
manner. One gram is dissolved in 30 c.c. of ether and extracted 
twice with seminormal aUcali, the aUcaline solution being washed 
with ether and the ethereal liquids combined. The ethereal 
residue is dried and weighed. This residue, cinnamein, should 
have a saponification value of 235 or over. 

There is on the market a certain amount of artificial balsam of 
Peru, which is of far less odom- value than the natural balsam. 
It is stated (British Pharmaceutical Codex, 1923, p. 173) that 
this can be detected by the following reaction. Two grams of 
the sample are shaken with 10 c.c. of petroleum spirit, and the 
petroleum solution is evaporated in a porcelain dish. The residue 
is dried on a water bath, cooled, and mixed with 2-5 c.c. of nitric 
acid of specific gravity 1-38. The pure balsam gives only a golden 
yellow colour. Dieterich (“ Analysis of Resins,” Scott, Greenwood 
& Co., London) gives the following values for three samples of 
' authentic origin : — 

/ 1 



Acid value . 




Ester value . 




Saponification value 




Cinnamein . 

71-4 per cent. 

77-6 per cent. 

73-6 per cent. 

Resin esters 

15-7 „ 

13-2 „ 


Insoluble in ether 

^•38 „ 

4-31 „ 

3-57 „ 

BALSAM OF TOLU. — ^Balsam, of tolu is an aromatic, 
fragrant resinous material obtained . from artificially -made in- 

67 ■■ 5-2 


cisions in the trunlc of Myroxylon idluifera, a tree indigenous to 
New Granada. When in the fresh condition it is a soft, tenacious 
mass, which becomes harder on Iceeping, and is in cold weather 
quite brittle. A fragment warmed and pressed on to a microscopic 
slide by the cover glass exhibits crystals of cinnamic acid under 
the microscope. 

It contains the benzoic and cinnamic esters of benzyl alcohol, 
free cinnamic and benzoic acids, traces of vanillin, and esters of 
a complex alcohol which has been named tolm-esinotannol. A 
very small amount of an essential oil is also present. 

Balsam of tolu is adulterated, either by the addition of other 
resinous matter, or by the abstraction of some of its odorous 
constituents. A pure balsam should yield not less than 90- 
98 per cent, of soluble matter to 90 per cent, alcohol, and under 
10 per cent, to jretroleum spirit. 

A pure balsam, should jdeld a distinctly crystalline residue to 
carbon bisulphide. This residue should Aveigh at least 25 per cent, 
of the weight of the sample. 

Common rosin may be detected by exhaustmg 5 grams AA'ith 
petroleum ether and shaking the filtered solution with an equal 
volume of a 0-1 per cent, solution of acetate of copper.’ In the 
presence of colophony the petroleum ether Avill be coloiu'ed a 
brilliant green, due to the soluble copper salt of abietic acid. 

A genuine balsam of tolu should have an acid value from 92 
to 135, and an ester value of 59 to 91. 

Delphin {Svenslc. Pharm. Tidskr., 1907, 3, 415) recommends 
the folloAving method of anatysis. Taa^o grams are dissolved in 
25 c.c. of ether, and normal solution of KOH is added. After 
shaking, the aqueous liquid is run into a flask, the ether v^ashed 
with a httle water, and the Avash Avater added to the original 
aqueous liquid. The ethereal solution is OA’^aporated on a water 
bath and exposed over sulphuric acid in a desiccator for eighteen 
hours, and Aveighed. This gives the cinnamein, Avhich should be 
not less than 8 per cent. The aflcahne liquid is treated AAuth sodium 
bicarbonate until an abundant precipitate is formed, and a 
current of COo is run tlirough the liquid for an hour. The solution 
is filtered, and the precipitate Avashed Avith Avarm AA^ater to remove 
aUcali. This precipitate is dried to constant Aveight, and gives the 
resin esters. The filtrate from the resin esters is treated AAdth 
6 to 7 c.c. of hydrochloric acid, and the resin acids collected on a 
tared filter, washed with water, dried and weighed. The weight 
should not exceed 1 per cent. The filtrate is extracted Avith ether 



and the ctliereal extract titrated with decinormal potash, with 


phenoljjhthaleui as indicator. One cubic centimetre of -J q alkali 

corresponds •Rith 0-014S gram of cinnamic acid, which should be 
present to the extent of 25 per cent, at least. 

According to Cocking and Kettle (see P. cfc E. 0. R., 1918, 202), 
the method of the British Pharmacopoeia, 1914, for the estima- 
tion of the balsamic acids in balsam of tolu is unsatisfactory, as 
much of the aromatic acid present is combined with resin alcohols 
and is insoluble in, and thus not extracted b}’’, carbon disulphide. 

In 1914 the authors described a process for the evaluation of 
benzoin by which the balsamic acids could be separated from the 
resinous matter, and the free and combined benzoic and ciimamic 
acids determined {Year Boole of Pharmacy, 1914, p. 355), and 
this process is now modified to meet the case of tolu balsam. 
Boiling out of the aromatic acids vTith magnesium oxide and 
water, in the presence of a small quantity of xylene to soften the 
resmous matter, was found to be the most satisfactory way of 
dealing vith the balsam. The magnesium salts of the aromatic 
acids are readily soluble in cold water, those of the resin acids 
being insoluble. A complete separation is effected, and the 
aromatic acids are obtained in a pm’er condition than by aqueous 
extraction alone. 

The mode of procedure is as follows : — 

(1) Free Balsamic Acids. — ^Five grams of the balsam are 
dissolved in 25 c.c. of hot alcohol in a 250 c.c. COo flask, 5 grams 
of light magnesium oxide and 20 c.c. of xjdene are added, and the 
flask shaken round until the contents are well mixed. One 
himdred cubic centimetres of water are now added, the flask 
connected to a reflux condenser, and boiled for one hour. After 
coolmg, the whole is poured on a Buchner Alter, and the aqueous 
portion of the filtrate separated from the xylene layer, which is 
returned to the flask together with the Alter paper and adhering 
magnesia-balsam magma. A second 100 c.c. of water is added 
and the flask again boiled for an hour, when the aqueous portion 
is separated as before and the extraction carried out a tliird time. 
The bulked aqueous liquids are washed once with 20 c.c. of ether, 
then rendered acid with hydrochloric acid, and the precipitated 
acids extracted by shaking out with ether. The greater part of 
the ether is distilled off, and the residual aromatic acids dried in 
vacuo over sulphuric acid, and weighed. 

(2) Total Balsamic Acids. — 2-5 grams of the balsam are saponi- 



fied by boiling with excess of alcoholic potash ; most of the alcohol 
is then evaporated off, the residue dissolved in 100 c.c. of hot 
water, and sufficient hydrochloric acid added to render the whole 
slightly acid. Five grams of light magnesium oxide and 20 c.c. 
of xylene are next added, and the whole boiled up under a reflux 
condenser for one hour. The aqueous Hquid is separated, the 
extraction twice repeated, and the buUced aqueous liquids treated 
as in the case of the free balsamic acids. 

The proportion of cinnamic acid is determmed by the gain in 
weight on bromination, details of which may be found in the 
previous note [Year Booh of Pharmacy, 1914, p. 355). .. 

The aromatic acids obtained from balsam of tolu are not quite 










Per cent. 
Free Ben- 
zoic Acid, 

: Per cent. 
Free Cin- 


Per cent. 

Per cent. 

Per cent. 










I 11-99 
















8-48 1 

> 11-86 







7-8 ’ 

' 10-69 








9-1 j 






92-2 ! 



6-63 1 








167-2 1 









































124-3 ! 














85-3 1 






so pure as those from benzoin. The brominated acids from tolu 
are slightly brown in colour, and contain a substance which is 
extremely pungent and lachrymatory. 

Balsam of tolu, as a rule, contains very little that is not soluble 
in alcohol, but occasionallj’’ samples are met mth containing 
woody matter. Three sucli samples contained l-G, 8-9, and 9 per 
cent, of insoluble matter. 

Moistm’e, generally present, was estimated by spreading in a 
thin laj^er on a sheet of glass and drying in vacuo over sulphuric 
acid. Amounts varying from 2 to 8*6 per cent.. were found, and 
the dried balsam was usually quite brittle. 

The determination of the acid value of the balsam is somewhat 



difficult, ou’ing to the dai’k colour and to the precipitate wliich is 
formed on running in the alcoholic potash. We find it best to 
proceed as follows : — 

Dissolve 5 grams of the balsam in about 50 c.c. of boiling alcohol, 
add a large quantity of phcnolphthalein solution — 3 or 4 c.c. — 
titrate the hot solution ■ndth normal alcoholic potash until the 
colour becomes dark brown (but not red), then attach to a reflux 
condenser, boil uj) for a few minutes in order to break up the 
precipitate, and finish the titration. 

By this method titrations agree to about 0-2 c.c. 


j KOH. 

The variations from a large number of samples of balsam 
examined during the last few years ai'c shown in the table on 
p. 70. 

Excluding numbers 11 and 12, which, from their low content of 
balsamic acids, are probably sophisticated, the figures indicate a 
range of — 

92-2 to 132-4 for acid value, 

69-3 to 90-9 for ester value, 

154-8 to 208-7 for saponification value, 
and 32-68 to 47-50 per cent, of total balsamic acids. 

The pharmacopoeial limits for acid value are from 107-4 to 
147-2, and for saponification value 170 to 202. 

Judged by these figures, numbers 3, 4, G, 7, 8, and 9 would be 
rejected for low acid values ; also the saponification values of 
numbers 6, 7, 8, 9, and 13 lie outside the limits, although the 
poorest of these balsams contains 33-87 per cent, of balsamic 
acids. On the other hand, numbers 11 and 12, though abnormally 
low in balsamic acids, would bo admitted as genuine. 

BANDOLINE. — name given by Erench perfumers to sub- 
stances used to -keep the hair fixed when it has a tendency to 
straggle.” They are usually perfumed mucilages, preferably of 
gum tragacanth, but sometunes of gum arable or quince mucilage. 
As they are liable to decompose, a little salicylic or boric acid is 
usually added to preserve them. 

DARIUM-- sulphate. — ^T his substance, Imown as barytes, 
and also as blanc fixe,’' is used to a small extent in some 

of- the cheaper types of face powders or enamels. It occurs 
naturally as a mineral, but as it must be in an exceedingly fine 
state of subdivision for use in the perfumery industry, the natural 
substance is not so suitable as an artificially precipitated sulphate, 



wliich is obtained as an impalpable powder. One of the most 
suitable forms of this article so far as this point is concerned is the 
by-product obtained in the manufactm'e of hydrogen peroxide. 

BAROSMA VENUSTA, OIL OF.— From the leaves of 
Barosma vennsta Goulding and Roberts {Jour. Clicm. Soc., 106, 
2613) obtained 2 per cent, of an essential oil having an agreeable 
aromatic odom’. It contains m 3 n’cene, estragol, linalol, aldeh 3 '’des, 
sesquiterpenes, and a small quantity of esters and phenols. It 

has the folloving characters : — 

Specific gravity ..... O-SGo 
Optical rotation . . . . +0° 47' 

Acid value ..... 5-6 

SajDonification value . . . 6-2 

Saponification value (after acetylation) 55 

BASIL, OIL OF, — Sweet basil oil is distilled from the entire 
fresh plant Ocimuui hasilicum. It is a plant of the N.O. Lahiaics, 
growing in Europe, northern Africa, Reunion, Java, and Algeria, 
etc. The oil is of a fragrant odour, and is of use in the preparation 
of perfumes of the types of violet, mignonette and jonquil, etc. 

There are several varieties of the plant, wliich has been veiy 
completely investigated bj’' E. G. and C. Camus {Bour e-Bertrand 
Fils, Bulletin, October, 1910, 23). Of these the most suitable for 
cultivation is the variety Crispum, The following are representa- 
tive characters of the oils from the principal varieties : — 






Thyrsiflorum . 


- 11° 




— 10° 


Album .... 


— 13° 




- 14° 


A normal oil distfiled in Europe (French or German) has a 
specific gravity 0*900 to 0*930 ; optical rotation, — 6° to — 20° ; 
refractive index, 1*4800 to 1*4960 ; and ester value, up to 12. 
Basil oil from Mayotte has a specific gravity 0*960 to 0*967, and 
optical rotation about -j- 1°. Basil oil from Java has been obtained 
by distilling the large-leaved variety, which is known locally as 
Selasih melcaJi. It contained about 30 to 40 per cent, of eugenol. 
A sample distilled in the Seychelles {Bidl. Imp. Inst., xvi., I., 30), 
had a specific gravity 0*962 ; optical rotation, + 0° 50' ; refractive 


P B R F U iU E Ji 3’ 

index. 1-.31-J0 : and ester mimbcr, 2-5. The European distilled oil 
contains methj-l-cliavicol (estragol), linalol, cineol, pinene, and 
camphor. Besides the above, several other species of basil yield 
fragrant essential oils, of which the following are the pimcipal 
Ochrtimi caiunii is a native of Madagascar, East Indies, Cliina, 
and Brazil. A sample of the oil distilled from material grown at 
Dakalba (Ivory Coast) has been examined by Bourc-Bcrlraml 
Fils {Bulletin, October, 1913, IS). It is an oil of pleasant odour, 
and is somisolid at ordinary temperatures. It has the foUov ing 
cliaractcrs : specific gravity at 32°, 1-033 ; optical rotation, 
— 2° 30' ; and saponification value, 301. Its cliief constituent is 
jnethj'l cinnamate, which causes the crystallisation of the oil. 
Ocinnnn gi'atissiviuvi is a native of Bengal, Chittagong, Nepal, and 
the Dcccan. It is a plant whose leaves have a remarkably pleasant 
-lemon odour. It is found in native gardens and round about the 
temples of the natives. It is found also on the Ivorj' Coast, and 
a sample distilled at Dakalba, and examined by Boui'e-Bcrlrand 
Fils {loc. cit.), was found to have a specific gramty 0-910, and 
optical rotation 1°. It contains thymol and carvacrol. A 
sample distilled in the Seychelles {Bull. Imp. Inst., xvi., 1, 30) 
had a specific gravity 0-995 ; optical rotation, — 14° ; and 
refractive index, 1-5200. A sample of the oil from tliis species 
has also been reported on by the Imperial Institute {Bulletin, 
vol. xxii., 3, 1924), and found to have the following characters : 
Sx}ecific gravity .... 0-996 

Optical rotation .... 

Befractive index .... 1-5320 

Phenols 55 per cent. 

and, according to Roberts {Jour. Soc. Cliein. Inch, 1921, 40, 
164, T.), had the following composition : — 

Terjjcnes, prmcipaUy ochnene . . 10-0 per cent. 

Phenols (eugenol) . . _ . • 55-0 

Phenol ethers (as methyl-chavicol) . 5-6 

Alcohols (linalol 1) ... . 13-0 

Esters as linalyl acetate . . .0-6 

Undetermined . . . . .9-8 

The fruits of 'Ocinium Aniericanum, from South Africa, were 
distilled, and the oil examined at the Imperial Institute {Bxilleiin, 
vol. xxii., 3, 1924). It had a specific gravity 0-953 ; optical 
rotation, -|- 2-75° ; and refractive index, 1-5110 at 24°. 

Goulding and PeUy {Bull. Imp. Inst., 1908, vi., 209) have 
examined the oil from Ocinium viricle, distilled in Sierra Beone. 
It had a specific gravity 0-911, and optical rotation + 1° 30'. 



It contained from 32 to 65 per cent, of thymol, 30 to 40 per cent, 
of alcohols, and a small amount of esters and terpenes. 

Glichitch {Bull. Soc. GMm., 1923, iv., 33, 1536) reports on two 
oils from Ocimum viride, one distilled in Grasse, and the other in 
New Caledonia. The Grasse oil, which was obtained to the extent 
of 2-588 per cent,, was a golden-yellow oil having an odour of 
thymol. It had a specific gravity 0-9104 ; refractive index, 1-4962 
at 22° ; optical rotation, + 0-9° ; esters, 1-96 per cent. ; total 
alcohols, 32-53 per cent. ; and phenols, 38 per cent. 

The oil from New Caledonia had a specific gravity 0-9235 at 
25-5° ; refractive index, 1-4945 at 22° ; optical rotation, -j- 1-5° ; 
esters, 0-73 per cent. ; total alcohols, 26-34 per cent. ; and 
phenols, 18 per cent. 

Roure-Berirand Fils {Bulletin, October, 1912, 71) have examined 
two samples of oil of basil from Mayotte. The odour of these oils 
was good ; it recalls, besides that of estragol, a somewhat distinct 
odour of anethol. They appear to have been prepared under 
favourable conditions. The first of these samples was of brownish 
colour ; the second was almost colourless. 

Their characters were as foUow : — 



Specific gravity at 15° C. . 



Optica] rotation 

+ 0° 58' 

+ 0° 56' 

Solubilit}'’ in 80 per cent, 

3 vols. and over. 

3’2 vols. and over. 

Acid value 



Saponification value 



Esters (as linalyl acetate) . 

1-9 per cent. 

2-2 per cent. 

These oils differ from the oils of basil of Grasse or Bourbon in 
their dea^iro-rotation and their high specific gravity. 

The so-called holy basil is Ocimum sanctum. It is common in 
India, where it is known as Tulsi or Tulasi. It is venerated by the 
Hindus, as the vervain was amongst the Homans. The worship 
of the plant is expounded in a book entitled “ Tulaskiava 9 am,” 
which contains a hymn in honour of the plant. The oil from the 
leaves has been examined by Bacon {Philippine Journal of Science, 
1910, 5, 261), and found to have a specific gravity 0-952 at 30°, 
and refractive index 1-5070. It contains methyl-chavicol, cineol, 
and linalol. Ocimum pilosum is an Indian plant known as Bdbooi- 


PEB F U M E B }* 

in Bengal and tlic ncighbonrlioocl. Bliaduri {Jour. Ainer. 
Ch-cm. Foe.. 1!U J, 36, 1772) has examined the oil distilled from the 
whole herb. It is a pale yellow oil containing limonene, citral, 
citronellal, cineol, and thj’inol, but no meth 3 d-chavicol. Its 
specific gravit}' is 0'SS7 at 25''; optical- rotation, — 3'7° ; and 
refractive index, 1-4840 at 25°. 

Ocivnnn imnivnnn, the dwarf basil, yields an oil containing 
about 14 per cent, of eugenol, and probably linalol. Its specific 
gravity is from O-SOO to 0-910 ; optical rotation, — 11° to — 14° ; 
and ester value about 12. 

BATH SALTS. — Bath salts, or bath cr 3 ^stals, are practically 
invariably composed of sodium carbonate, with, occasionallj^, the 
addition of a little borax. The use of bath salts does, in fact, 
soften hard water in which much lime exists, but the}’’ are 
actualh’ used rather as an attractive vehicle for perfume in the 
bath. Sodium carbonate, NaoCOg -h lOHoO, in crj’stals of size 
according to taste, is the base of nearly all bath salts, the fine 
cr 3 \stalline so-called sodium sesquicarbonate being rarely obtain- 
able to-da 3 \ They are usuall}’’ tinted with a coal-tar colour, 
generall}’’ basic colours, which are spra 3 ’ed in solution on the 
crystals, or the carbonate may be immersed in an alcoholic solution 
of the d 3 ’e, drained, and dried. In perfuming the cr 3 "stals, per- 
fumes should be chosen which are not affected b}’’ alkalies, as 
otherwise a more or less speedy decomposition of the perfume ■will 
take place. As sodium carbonate is liable to effloresce, a little 
glycerine is often added to the crystals to counteract this tendenc 3 ^ 
Bath powders and water softeners are usually merel}’’ powdered 
dried sodium carbonate, with or without a little borax, coloured 
and perfumed to taste. A little perborate of sodium is sometimes 

BATTEUSE. — ^This is the name given to a machine, in 
France, used for beating up a pomade or concrete with alcohol 
to prepare an alcoholic solution of their odorous substances, either 
for a finished product such as a “ triple extract,” or for further 
conversion into an “ absolute.” 

BAY, OIL OF. — Bay leaves, from which the West Indian 
bay oil is distilled, are, principally, the leaves of Pivicnta acris 
{Mtjrcia acris), but no doubt other closely allied species are from 
time to time mixed with them. The tree is a handsome one, 
growing to the height of 20 to 40 feet, of pyramidal form. In the 
woods of Antigua, Janiaica, and Barbadoes the fragrance of these 


P E i? E U 31 E n Y 

trees permeates tlie atmosphere, so poAverful. is the odom’ of the 
essential oil contained in the leaves. The leaves yield from 1 to 
1*0 per cent, of essential oil, which contams constituents of such 
difl'ercnt specific gravities that the oil is often collected in liglit 
and heavy fractions in such an erratic mamier that the com- 
mercial oil is frequently nothing more than a fractionated oil of 
varying richness in phenols — ^the characteristic odour hearers of 
the oil. Tliis has caused a determined effort on the part of the 
authorities to place the industry on a sound basis, and to ensure 
the manufactm’e of an oil of comparatively constant composition. 
These experiments commenced in 1908, and Su’ Francis Watts, 
the Commissioner of Agriculture for the West Indies, states that 
the results obtained from the experimental plot then established 
showed that the cultivation of the tree was a matter worthj^ of 
the attention of inhabitants of the islands having uncultivated 
land at their disposal. Trees were planted in 1908, and distillation 
commenced in 1911, the leaves jdelding practically 1 per cent, of 
oil. By 1913 the actual yield of leaves had nearly doubled, and 
these also jdelded a higher percentage of essential oil. He also 
states that experiments in Montserrat and Antigua show that the 
specific gravity and phenol content of the essential oil are 
influenced considerabl}'^ by the character of the leaves collected 
for distillation, especiaUj^ as the use of immature leaves lessens 
the amount and value of the oil. 

Assuming that the distillation has been carried on satisfactorily 
and the whole of the oil obtained has been bulked, a normal West 
Indian bay oil has the following characters : specific gravity, 0-9 65 
to 0'98o ; optical rotation, — 0° 30' to — 4° ; refractive index, 
1-5100 to 1-5250 ; and phenol content from 55 to 70 per cent. 
But if the oil is not so distilled, very different results will be 
obtained. To indicate the differences so obtainable, 150 lb. of 
leaves were distilled in the Government laboratory at Antigua, 
and the oil coming over at intervals of about an hour each was 
examined, •odth the following results ; — 




Phenol content. 
Per cent. 

1 . 


. 0-8669 


2 . 

. 0-9241 


3 . 

. 1-0259 


4 . 

. 1-0381 


5 . 

. 1-0409 


6 . 

. 1-0432 


n . 

. 1-0434 


9 . 

. 1-0436 


7 « 


The oil obtained in the first hour amounted to nearly half of 
the whole quantity. 

The unsatisfactory variations in the commercial oil, which have 
not 3^et disappeared, are explained in the account given by 
Professor Maiicoe [Pliarm. Jour., [3] viii., 1005), who thus describes 
the process : “ The apparatus used in distilling the oil was a 
200-gallon copper still heated by steam, so arranged that either 
wet or dry steam could be used at pleasure. From 200 to 300 lb. 
of leaves vrere used at each running of the still, and to work off 
tills quantity required from eight to twelve hours, during which 
time from SO to 100 gallons of distillate would be obtained. The 
oil comes over in two portions. Fh'st, a portion lighter than 
water, that comes over veiy rapidly, and then the heavy oil, that 
comes over veiy slowly and does not easity separate from the 
water, vdth which it forms a milk}’’ emulsion. The following 
notes were made of one of the runs with 200 lb. of leaves. The 
distillate was collected in quantities of 2-1 gallons of the water 
carefully separated from each portion. The light oil came over in 
the first 15 gallons of distillate, from which it promptly separated, 
leaving the water quite clear. The specific gravity of each of the 
six portions was as follows : 0-870, 0-930, 0-94C, 0-9G4, 0-982, 
0-990. The distillation was then continued to obtain the heavy 
oil until 65 gallons more of distillate were obtained. This oil was 
received in three portions, and the specific gravity of each portion 
then taken : 1-023, 1-035 and 1-037.” 

An oH of bay distilled in Fiji has been examined at the Imperial 
Institute and found to contain only 23 per cent, of phenols, in 
spite of a specific gravity 0-961, but to bo ver}’- rich in phenol 
methyl -ethers. 

Oil of bay contains pinene, and probably dipentene, together 
with its principal constituent, eugenol, and its methyl ether. 
Chavicol, methyl-chavicol and citral are also present. Power 
and Kleber do not agree that pinene and dipentene are present, 
but consider the only terpene in the oil to be phellandi-ene. These 
chemists also detected a small quantity of the olefinic terpene, 
myreene, in the oil. 

The odour of the oil is typically phenolic, but differs from that 
of oil of cloves or oil of pimento on account of the presence of its 
subsidiary constituents. 

West Indian bay oil forms the basic perfume for bay rum {q.v.). 

The Californian bay is an entirely different tree from that 
described above. It is Umhelhilarirt CaJiforuiccf., often known as 



the mountain laurel or the Cahfornian oHve. This tree has 

ighly odorous leaves, which yield an'essential oil which, according 
to ;^wer and Lees, contains as its principal constituent a ketone, 
C 10 H 14 O, which they have named umbellulone. The oh contains 
a small quantity of eugenol, 20 per cent, of cineol, and 10 per cent, 
of eugenol methyl ether. It has a specific gravity 0-950, optical 
rotation - 3G°, and refractive index 1-4833. 

MAYBERRY. ^The hayberr}’-, candleberry, or wax mju-tle of 
JNorthern America is Myrica cerifera, a branching shrub of 4 to 
8 feet m height. It yields a fragrant essential oil having a specific 
gravity about 0-917, optical rotation — 1 ° 30', and refractive 
index 1-4990. It resembles the oil from the leaves of the bog 
myi-tle (q.y.). The berries also jdeld a wax of considerable value, 
and practically identical with bog myrtle wax. It burns in candle 
form, vdth a very white flame with very little smoke, and gives 
off a very agreeable odour. There are several alhed species of 
Ihjnca indigenous to South Africa, which yield a myrtle wax. 

BAY RUM. Bay rum is a very highty esteemed toilet pre- 
paration, used in general as a hair wash or as a lotion spra 3 ^ed on 
the face after shaving. The preparation was originally sent from 
the West Indies to this country, and this imported article was 
liigWy esteemed. It is probable that it was originally a distillate 
of rum Tidth the bay leaves, but Jater a mixture of bay, pimento 
and cloves was used. To-day very little bay rum is imported, 
as every perfumer manufactures his ovm according to liis own 
private formula. The use of rum as the solvent has now almost 
entirely disappeared, and the best bay rum is now made from 
alcohol and the various essential oils containing eugenol, bay oil, 
of course, predominating. Terpeneless oils have been recom- 
mended for this pm-pose, and may effect a slight economy in 
alcohol, but as most of the oils concerned — ba 3 ^, pimento, cloves, 
and cinnamon leaf— are very rich in phenols, the use of the 
terpeneless oils is probabl 3 ^ more expensive than filtering off the 
small quantity of insoluble constituents. 

Cheap bay rum is made with meth 3 dated spirit, fm-ther de- 
natured by the addition of extract of quassia. This must not be 
done, however, without the permission of the Customs authorities. 

suggestion of the presence of rum is sometimes given by the 
addition of an artificial essence of rum. This is, in its best 
varieties, a mixture based on an impure eth 3 d acetate made from 
crude p 3 T’ofigneous acid. 



BDELLIUM is a somewliat aromatic rcsin which has a resem- 
blance to myrrh, and is often found in admixture with it. It 
occurs as African bdellium and East Indian bdellium. It is the 
product of various species of CommiphoTa and Balsamodendron. 
It can be distinguished from m3rrrh by its not yielding the 
characteristic reaction with nitric acid. This reaction is as 
follows. The gum resin is extracted with ether and the ether 
evaporated. The residue is brought into contact with the fumes 
of nitric acid. Genuine myrrh gives a violet colour, which is not 
the case with bdellium. 

Bdellium contains about 75 per cent, of resin soluble in alcohol. 
The following figures for bdellium are due to Dieterich ; — 

Acid value. 

Ester value. 















J J 



Indian . 



3> • 



(See also under “ Incense.”) 

BEESWAX. — ^Beeswax is used by the perfumer in the manu- 
facture of cold creams and similar preparations. Natural or 
yellow beeswax, the Gei'a flava of pharmacy, is the substance 
secreted by the hive bee, Apis melUfica, and probably other 
species, to build up the skeleton of the honeycomb. After the 
honey has been extracted, the wax is melted with water, separated, 
and strained. Beeswax varies from pale yellow to deep brown in 
colour, this feature depending largely on the food of the bees. 
It is hard, solid, not very unctuous to the touch, and breaks "with 
a dull granular fracture. It has an agreeable honey-hlie odour. 

The natural beeswax is bleached to a clean white coloirr, either 
by exposing it in thin layers to the action of air, moisture and 
sunlight, or by treating it with chemicals such as dilute chromic 
acid. Chemically-bleached beeswax is more brittle ^an air- 
bleached wax, and retains traces of acid, which renders it rather 
less desirable for perfumery purposes than the air-bleached variety. 
Pure beeswax should have the following characters : specific 
gravity at 15°, from 0*958 to 0*968 ; melting point, 61° to 64° ; 
refractive index at 80°, from 1*4380 to 1*4420 ; acid value, 16*5 
to 22*5 ; ester value, 68 to 78 ; and saponification value, 85 to 



100. Chemically-bleached wax may have a slightly higher acid 
value than that given above. 

The principal adulterant of beeswax is ceresine or paraffin wax, 
which are far less expensive. Sometimes stearic acid and carnauba 
wax are used as adulterants, though this is but rarely the case 

BELLARY LEAF OIL. — The leaves of Litsea. zeylanica 
yield about 0-6 per cent, of an odorous essential oil of specific 
gravity 0-890 ; optical rotation, -f 1-5° ; and ester value, 15. 
It is an Indian essential oil, which has not, so far, been produced 
on a commercial scale for perfumery purposes. It probably 
contains geraniol (P. db E. 0. R., 1923, 14, 271). 

BENZALDEHYDE. — Benzaldehyde, CgHg.COH, is the essen- 
tial principle of the oils of almond, peach and apricot kernels. 
These oils contain little else but benzaldehyde, so that the 
artificially prepared substance is very commonly used in place of 
the natural essential oils. It is a highly refractive liquid, of 
specific gravity 1-052 ; refractive index, 1-5450 ; and boiling 
point, 180°. It rapidly oxidises to benzoic acid, so that it should 
be kept from exposure to air and moisture. The usual starting 
point in the manufacture of benzaldeh 3 ^de is the coal-tar hj^dro- 
carbon, toluene, which must be separated from accompanj’^ing 
impurities before it can be used for this purpose. It is heated, 
preferably in a briUiant sunlight, to boiling point, and a current 
of chlorine gas is passed through it until it has absorbed 40 per 
cent, of its weight. The benzal chloride CgHg.CH.Cl 2 so formed 
is mixed with three times its weight of water and its own weight 
of powdered challc, and the mixture heated for four hours to 
130° C. The mixture is then steam-distilled and the crude benz- 
aldehyde purified by conversion into its crystalline bisulphite 
compound (see “Aldehydes, Determination of”), wliich is 
rendered allcaline, and the liberated benzaldehyde steam-distiUed. 

Benzaldehyde so manufactured is invariably contaminated 
with organic chlorine substitution products. This fact renders it 
of little value if used for perfuming pale-coloured substances such 
as white soap, as products perfumed with it steadily darken in 
colour. Hence it becomes necessary either to eliminate such 
chlorine compounds or to manufacture a benzaldehyde free from 
chlorine by a process in which no chlorine is used. The following 
are examples of such methods. Three hundred kilograms of 
toluene are mixed vdth 700 kg. of 65 per cent, sulphuric acid and 



well agitated, udtli the gradual addition of 90 kg. of finelj’- powdered 
manganese dioxide, keeping the temperature at about 40°. Or 
300 Ivg. of toluene are mixed with 150 kg. of oxide of nickel and 
heated to 100° for six hours, by which a direct oxidation of the 
toluene takes place. 

Chlorine-free benzaldeh 3 'de is used as an adulterant of essential 
oil of almonds, but as samples of the so-called chlorine-free 
substance contain minute quantities of chlorine (which is not 
harmful for anj^ perfumery purpose), the detection of these traces 
of chlorine becomes imirortant, as there is a considerable diver- 
gence between the jrrices of the natural and the artificial products. 
Tire following simple method will detect chlorine when present 
in appreciable amount. A piece of filter paper about 2 inches by 
1 inch is rolled in the shape of a spill and saturated vdth the liquid. 
The paper is placed in a small porcelain dish, which stands in a 
larger dish, so that a glass beaker can be inverted over the smaller 
dish whilst resting in the larger one. The paper is set alight and 
the beaker, moistened with distilled water, inverted over it. When 
the flame is extinguished, the inside of the beaker is rinsed out 
with distilled water into the outer dish, the liquid, filtered and 
tested vith silver nitrate for chlorides. A turbidity or precipitate 
indicates the presence of an appreciable amount of chlorine. For 
the detection of veiy minute quantities Salamon recommends the 
following process. About 2 grams of the benzaldelyde are heated 
in a retort with 40 c.c. of concentrated sulphmic acid, and 5 c.c. 
of nitric acid in a small retort, and the fumes collected in a solution 
of silver nitrate until no fru4;her precipitate is obtained. The 
liquid is heated with dilute nitric acid, and the precipitated silver 
chloride separated and weighed. Tliis method will detect as 
little as 0-01 per cent, of chlorine. Voigt {Z. Angew. Cliem., 1922, 
35, 654) has described a combustion method wliich is tedious, but 
gives accurate results. 

BENZOIC ACID. — ^This acid, CgHs.COOH, is the simplest 
acid of the aromatic series. It is found to a small extent in the 
free condition, but principally in the form of esters {vide “ Ben- 
zoin ”). It is a crystalline substance melting at 121°, and having 
a slightly aromatic odom’ suggestive of vanilla. To obtain it 
fr6m benzoin the dry powdered gum is placed in a metal receptacle, 
covered with a filter paper pierced with pin holes, and covered 
with a paper hood. The powder is heated, and the benzoic acid 
sublimes and collects on the paper hood. It is prepared on a 
considerable scale artificially by the hydrolysis of the chlorination 
r- 81 6 

P E F U 21 E RJ 

product of toluene. It is emplo 3 ^ed largeh* as a preservative of 
fats, sucli as lard, etc, 

_ BENZOIN.— Benzoin, or Gum Benjamin, as it is often called, 
IS an important balsamic resinous material, much used in the 
perfumery industry, both on account of. its sweet heavy odour 
and Its useful fixative properties. It is used in the manufacture 
of incense. The earliest literature dealing with the subject speaks 
of benzoin as Lxiban Jawi (“incense of Java”), the name 

aya being used for Sumatra and other neighbouring islands. 

t IS easy to tiace the modern name through successive corruptions 
of the above name: banjavd, benjui, benzoi, benzoin, and 
benjamin. There are several types of benzoin, of which Siam 
benzom is preferred for perfumery purposes. This is the product 
of a tree not 3 ^et identified with certainty, but which may be 
Styrax Tonlinense. The trees do not produce the secretion 
normaUy ; a wound is inflicted in the bark sufficiently deep to 
mjure the cambium, which results in the formation of oleoresin 
ducts in which the secretion is produced. It is, in fact, a patho- 
logical secretion. When sufficiently hard and dry, the material 
is collected, either in the form of lumps or in small tears. The 
principal tynstituents of Siam benzoin are free benzoic. acid and 
the benzoic ester of the alcohol lubanol. There are also present 
siaresm 3 d benzoate, vaniUm, and traces of other aromatic sub- 
stances. The combined benzoic acid amounts to about 25 per 
cent., and the free benzoic acid to about 15 per cent. It should 
jpield 90 per cent, at least of extract to alcohol, and should not 
contain more than 2 per cent, of mineral matter. 

Beinitzer {Arch. Pharm., 1921, 259, 1 , 60) has isolated a smaU 
amount of siaresinolic acid from Siam benzoin. It is a crystalline 
substance of the formula C 30 H 48 O 4 , melting at 260°. He also 
fuUy examined the ester lubanol benzoate, C 17 H 16 O 4 , which he 
found to cr 3 ^stallise in plates melting at 72° to 73 °, Eor further 
details the papers above q^uoted should be consulted. 

Sumatra benzom is of weaker and less agreeable odour than 
Siam benzoin. It is derived from Styrax Benzoin, and owes its 
odour principally to the cinnamic acid esters of benzoresinol and 
benzoresinotannol. There are also present free benzoic acid, 

st 3 nol, benzaldehyde, vanillin, phenyl-propyl cinnamate, and 

Other varieties are those -known as Balambang, Padang and 
Penang, but they are not used in ‘ perfumery except for the 
manufacture of incense. 



Siam benzoin is esteemed b}' perfmners on account of its 
vanilia-like odom'. A full and interesting account of the history 
of benzoin by E. IM. Holmes -vdll be found in the Perfuviery and 
E-sscnfial Oil Record, 1916, 112, in which he gives the following 
details in regard to Siam benzoin, the method of collection being 
described in the Keio Bulletin, 1895, 195 ; — 

The season for collecting the benzoin is in July or August, 
when the work in the paddy fields is finished, till November. 
The trees arc notched with an axe, and the exuded soft resin is 
allowed to remain on the trees for three months to harden, so that 
the benzoin is read}' for sale in December. 

It is sorted into tluee classes. The best, or “ Sua,” is in large 
lumps, and is clean ; the second consists of smaller lumps, and 
has some bark attached to it, and is half the value of the first ; 
the third, or “ Musi,” is soiled with dust and dirt, and is in fine 
small pieces. It is collected by the Siamese Thai, Annamites, and 
Tongoos, who have settled in the province and carried on the 
work from time immemorial. This account is furnished by 
Siamese, not Eiuopean, observers. 

In 1910 an apotheker at Basle, Herr Hartman Rordorf, published 
an interesting account of the collection and preparation of Siam 
benzoin in the SchweizeriscJie WoJienscJirift, having fortunately 
been able to obtain information through his brother-in-law, Dr. 
Domeller Nieuwenhuis, the Dutch Minister in Siam, who lived 
some j’^ears in Bangkok. Great difficulty was experienced in 
obtaining information and specimens. Between 1907 and June, 
1910, ten expeditions were sent to obtain material, but all except 
the last proved imsuccessful. The road and paths in northern 
Siam are very bad, and the commercial traffic is chiefly carried 
by the rivers. At high water these are not navigable, and at low 
water are impassable swamps. The morasses are navigable only 
for a short period during the year. The period necessary to 
traverse them is three days before the benzoin-producing region 
can be reached. In this neglected district there is a settlement 
of small, long-haired people who collect the benzoin, and who 
apparently emigrated from China in very early. times. They speak 
an old forgotten language and wear different clothes from the 
natives of southern Siam. 

This method of coUecting the benzoin and preparing it for 
market is as follows : On trunks of 20 to 25 cm. in diameter, pieces 
of bark of rectangular shape from J to 4 handbreadths in size are 
loosened, and the resin runs out on the inner side of the bark, 


C — 2 


solidifying there Ijy the heat of tlie snn. This forms the finest 
qualit.y. Tlie smaller fragments are formed into lumps by hand. 
The resin is spread out on a strong mat in a heap, and gmger roots, 
first hollowed and filled with the marrow of the bone of the pig, 
are mixed uith it, and the mats are tied up at the ends into a 
bundle. The contents are examined from time to time to see 
if the fat has been taken up, and if not, fresh fat is^ used. It is 
-^aid that rancid fat uiU not, lilce fresh fat, pass through the ginger 
root. The process takes about a year, its object being to preserve 
a fine aroma. When the fat has disappeared from the ginger the 
drug is ready for export vithout risk of losing its fine odour 
through the long hot joirmey to Bangkok. The natives rub the 
gum resin with sugar and then make it uito an emulsion with 
^'-•ater. vrliich is highly prized as a wash and as an addition to 
baths. The specimen of Siam benzoin in the museum of the 
Pharmaceutical Society obtained from vdiolesale commerce in 
this country iDears out this description fairly well. In some 
specimens large tears of benzoin are attached to the inner .smlace 
of a moderately thick bark, and differ from the Sumatra land not 
only in the vanilla odour, but in the fact that the tears are 
unusually free from one another. It seems quite possible that 
this is due to their having an oily surface, caused bj’- the hog’s 
marrow, which would probabty prevent loss of benzoic esters to 
some extent and thus conserve the natm’al fragrance of the resin. 
It is interesting to record that Herr Hordorf has found resin canals 
to be abundantly present on the inner surface of the bark {Pliarm. 
Jour. (4), 31, 515). 

The most recent contribution to the knowledge of the tree 
yielding Siam benzoin was published in 1913 in the Axiothelcer 
Zcihing, by Dr. C. Hartwich, who received specimens of the 
matiure fruit as well as leaves, bark and resm from Messrs. Bilder- 
meister and Schoch Bilhviller from San Hua, which is nearly in 
the centre of the Siam benzoin district, between Luang Phrabang 
and Hanoi. 

Dr. Hartwich beheves that the produce of this district passes 
through the tovui of Luang Prabang into Siam, since Thorel 
reported in 1866 that the benzoin was collected on the mountains 
between Laos and Tonldn, in latitude 19 N., in the forests of one 
of the affluents of the east of the Mekong River on the frontier 
of Armam. The sample of Siam benzoin received by Dr. Hartwich 
was white internal^ and brownish externally, and 3delded no 
cinnamic acid, and the fruits were oval, as might have been 



expected from Tliorel’s herbarium s25ecimens above mentioned. 
The mature fruits were submitted to the Ro 3 ’-al Gardens at Kew 
for identification, and vere there determined by Mr. Craib to be 
identical with the Anihoslyrax Tonldnense of Pien'e and the Styrax 
rnacrotliyrsus of Perkin. 

B_v the rules of priority*, Perkin's name comes first, but as 
Anihoslyrax is regarded at Kev as a sub-genus onlj’-, IMi-. Craib 
has named the tree Styrax Tonldnense. The fruit is elliptical, 
smootli, vith a thin pericarji dehiscing longitudinally into three 
valves, and an ellijDtical, oval, dark brown seed, which is rough 
with minute papillae. It is thus quite different from the fruit of 
S. Benzoin, which is globular, nearly an inch in diameter, with a 
thick pcricaiq), which is indehiscent. 

Another sjeecies of Styrax, S. henzoicles, Craib, is rejeorted to 
j'ield benzoin near Chieng-mai, in Siam, but the resin does not 
possess the same apjeearance as the Siam benzoin of commerce, 
and is probabl,y onlj" used locall 3 \ It ma 3 ’- therefore be con- 
sidered proven that Styrax Tonldnense is the botanical source of 
Siam benzoin. 

The following are average figures for benzoin of good qualit 3 ’-, 
free from admixture with earth 3 ’’ matter, etc. : — 

j Sinni. 



I Sumatra. 


Other varieties. 

' Under 2 per cent. 
Soluble in 90 per i 

1 Under 2 per cent. 

Under 3 per cent. 

cent, alcohol . '90-96 

1 90-94 


Acid number . j 130-15S 

1 98-140 


Ester number . ' 42-69 

1 I 



Cocking and Kettle, in a paper read before the British Pharma- 
ceutical conference at Chester in 1914, gave the following com- 
plete anal 3 \ses of eleven samples of Sumatra and Siam benzoin 
(see p. 86). 

If Sumatra benzoin be warmed with chromic acid mixtime, a 
strong odour of benzaldehyde is given off, owing to the oxidation 
of cinnamic acid. This distinguishes it from Siam benzom. 
According to Muter, Siam benzoin gives the following character- 
istic reaction. If the dried petroleum ether extract of the resin is 
treated with sulphuric acid, a cherry red colour is developed. It 
is frequently of importance to determine the amount of benzoic 
acid in benzoin. This can be done b 3 '^ digesting 10 parts of the 




takablo odour of beiizaldehyde was produced. 




powdered gum with 6 parts of slaked lime and 100 parts of water. 
After sis hours the liquid is boiled, filtered, and the residue 
washed. The filtrate is concentrated, acidified with hydrochloric 
acid, and well cooled. The precipitated benzoic acid is filtered 
off, washed with a little water, and dried between porous paper. 
The small amount of benzoic acid left in the mother liquor is 
extracted with chloroform and dried in a desiccator and weighed. 
To estimate the total balsamic acids, Cocking and Kettle give the 
follovdng process : Five grams are extracted, with alcohol in a 
Soxhlet tube and the extract hydrolysed with alcoholic potash. 
The alcohol is evaporated, the residue dissolved in 100 c.c. of 
water and rendered faintly acid with hydrochloric acid, and then 
6 grams of magnesia and 20 c.c. of xylene added. The whole is 
boiled under a reflux' condenser for an hour, cooled, the aqueous 
liquid filtered off, and the insoluble matter boiled twice with 
100 c.c. of water, which is allowed to cool before being filtered. 
The combined aqueous extracts are extracted once with ether, 
then acidified with hydrochloric acid, and the liberated balsamic 
acids shaken out with ether. The ether is evaporated and the 
residue dried in vacuo over sulphuric acid and weighed. 

In the manufacture of incense powdered benzoin always plays 
an important part (see " Incense ”). There is also a plant known 
as Benzoin odoriferum {Laurus henzoin), commonly termed spice 
wood or wild allspice, which grows in various parts of North 
America. Nearly every part of the plant yields an aromatic oil, 
that from the bark probably containing cinnamic compounds. 

BENZOPHENONE. — Benzophenone, or diphenjd ketone 
CeHg.CO.CoHg, is a fragrant crystalline body, melting at 48° 
and boiling at 307°. Its specific gravity at 50° is 1-098. It is 
prepared by distilling calcium benzoate or by the condensation 
of benzene with benzoyl chloride in the presence of- aluminium 
chloride. It is useful in the preparation of heavy odoms of the 
so-called Oriental type. 

BENZOYL ISOEUGENOL. — ^This body is a substituted 
isoeugenol of the formula C6H5.CH2.(C9 H:i 202). It forms small 
crystals melting at 59°, and has a slight odour. Its principal value, 
however, lies in its use as a fixative. It is recommended in the 
fixation of carnation, fern, rose and orchid perfumes. 

- BENZYL ACETATE. — ^Benzyl acetate is an ester of the 
formula CcHg.OHa.O.OC.CHg. It occurs naturally in oil of jasmin, 



oil of 3 'ltmg-ylangj oil of tuberose, and similar flower oils. Its 
odour is sweet, but not intense ; it is prepared synthetic allj’', and 
is indispensable in the preparation of artificial flower oils of the 
jasmin or ylang- 3 dang ty^pes. It is a colourless oil, soluble in anj'' 
proportion in 90 per cent, alcohol. Its specific gra^vity is about 
1-000 ; refractive index, 1-5034; and boiling point, 216°. It 
may be prepared by boihng for thirty hours a mixture of 5 parts 
of benz^d chloride, 4 parts of fused sodium acetate, and 4 parts 
of a glacial acetic acid. Excess of acetic acid is removed by 
distillation, and the ester is washed and rectified. It should be 
free from chlorine, as specimens containing more than faint traces 
tend to discolour soap, etc., which has been perfumed by this 

BENZYL ALCOHOL.— This body is the lowest member of 
the normal aromatic alcohols containing the benzene nucleus, 

It has the formula CgHj-CHoOH. It exists in the free state to a _ 
small extent in those oils which contain its esters, such as jasmin, 
tuberose, cassie flowers, jdang-jdang, etc. It is useful in the 
preparation of such artificial flower oils. It is an oil of specific 
gravity about 1-04S ; refractive index, 1-5400 ; and boiling 
point, 205° to 207°. 

It is useful to the perfumer not onty for its slight floral odour, 
but as a fixative, and also as a solvent for artificial musk. 

It maj’’ be prepared bj’’ mixing magnesium h 3 ^drate (1 molecule) 
with benz 3 d chloride (2-2 molecules) and adding about ten times 
the weight' of water. The mixture is maintained at 100° for some 
hours with continual shaking. The 3 deld is about 95 per cent, of 
the theoretical. 

BENZYL BENZOATE.— This ester, of the formula 
CpHg.COO CHa.CgHg, occurs naturallvj n balsam of Per u, and to 
a small extent in 3 dang- 3 dang, tuberose, and similar flower oils. 

It is, when quite pure, a ciystalliue solid meltmg at 21°. In 
commerce, however, the artificial ester contains minute quantities 
of unobjectionable impurities, which keep it hquid at ordinary 
temperatures, and the melting point seldom exceeds 18° to 19°. 

It has a specific gravit 3 ’' 1-1224, refractive index 1-5685, and boils 
at 323°. Its odour is very slight, but strong enough to be of 
value in reproducing floral odours. It is also a very useful fixative, 
and an excellent solvent for artificial musk. It should be free 
from chlorine. It is obtained commercially b3’' dissolving sodiuin 
in benzyl alcohol and heating it with benzaldeh 3 ’-de for twent 3 ^ 



four liours on a water bath. The mixture is acidified mth acetic 
acid, and the ester precipitated by water and rectified. 

BENZYL BUTYRATE. — Benzyl butjwate is an ester which 
has a softer odour than benzyl acetate, and is indisj)ensab]e in 
correcting the harshness of the latter in the best artificial jasmin 
perfumes. Its formula is CgHg.CHg.OOC.lCgH-). It has a 
specific gravity l-Olo, refractive index 1'4945, and boils at 242°. 

BENZYL CINNAMATE. — The cinnamic ester of benz 3 d 
alcohol, of the formula CgHj.CHo.COO.CH : CH.CqHj, is found 
as a natural constituent of storax, balsam of Peru, and balsam 
of tolu. It is a cr 5 'stalline substance with a characteristic sweet 
balsamic odour. It is prepared artificially bj^ heating sodium 
cinnamate, alcohol and benzjd chloride under a reflux condenser. 
It forms white crystals melting at about 32°. It boils at 195° to 
200°. It is used in the preparation of heavy odours of the Oriental 
type, and is also useful as a fixative. 

BENZYL CYANIDE.— This compound, CgHs.CHsCN, is a 
natural constituent of oil of neroli and of certain cress oils. It is 
a liquid of powerful odour, boifing at 231° and having a specific 
gravity 1-016. It is probablj’' an intermediate substance in the 
formation of phenjd-acetic acid in plants in which this acid occurs. 
It is an imj)ortant intermediate in the preparation of synthetic 
phenyl-acetic acid, and can be prepared b 5 '- the action of sodium 
cj’-anide on benzjd chloride. 

BENZYL-ETHYL OXIDE.— This oxide, of the formula 
OgHjCHo.O.CoHg, is a colourless oil, useful in perfuming soap on 
account of its resistance to alkafies. It has a penetrating fruity 

BENZYL FORMATE is an oil havmg an odom of jasmin. 
It is somewhat harsh in odour, and should be used in small 
quantities only. It maj’’ be prepared b 3 ’' the action of formic acid 
on acetic anh 3 ’’di’ide, and then esterifying benz 3 d alcohol vdth the 
mixed anliydride so formed. Benz 3 d formate boils at about 202°, 
and has a specific gravity 1-083, and refractive index 1-5195. 



BENZYL-METHYL-CARBINOL.— This body is a fragrant 
oil, isomeric ^vith phenyl-propyl alcohol. It boils at 215°, and has 
the formula CcH 5 .CH„.CH( 0 H)-CF 3 . 



BENZYL PROPIONATE. — Like the coiTesi3onding loutyrate, 
this ester has a softer and sweeter odour than the acetate, 
and is used to correct the harshness of the latter in artificial 
jasmin odours. It has the formula CcH6.CH2.00C(C2H5). It has 
a specific gravity about 1-0362 ; refractive index, 1-4980 ; and 
boiling point, 228°. 

BENZYL SUCCINATE. — This substance, of the formula 
(CgHg. 0112)2(000)2(0112)0, is a crystalline odourless powder 
meltmg at 45°. It is a useful fixative. 

BENZYL VALERIANATE. — This ester, of the formula 
OeH5.0H2.000.(04H9), is prepared by esterifjdng benzyl alcohol 
vith valerianic acid. It has an odour of valerian, and is used in 
minute quantities in a number of floral oils, such as artificial otto 
of rose. Its specific gra^nty is 0-996 ; refractive index, 1-4880 ; 
and boiling point, 250°. 


OO.OII3, ^ sweet floral odour. It is used to round off and 
modify artificial flower oils, but is especiaUy useful as a basic 
material for artificial sweet pea perfume. It is a crj^stalline body 
of specific gravity 1-0377, melting at 42°, and boiling at 260° to 
262°. It is prepared by mixing 22-5 kg. of acetone, 15 kg. of 
water, and 15 kg. of benzaldehyde. The mixture is cooled to 10°, 
and 9 kg. of 10 per cent, solution of caustic soda is slowly added, 
with constant stirring, care being taken that the temperatiu’e does 
not rise materially. The excess of acetone is removed by distilla- 
tion, and acetic acid added. The ketone is then steam distilled. 
According to Lewinsohn (P. dh E. 0. B., 1924, 118), a distinct 
improvement of the yield obtained by these methods results if 
allowance is made for the fact that -water is produced to the 
extent of 16 per cent, of the benzaldehj^de reaction mixture, this 
water causing dilution of the soda lye. The strength of the 
10 per cent, caustic soda solution can be maintained by the 
gradual addition of a 20 per cent, solution so as to counteract 
the dilution caused by the water produced in the reaction. 

The method of conducting the operation is as follows. In a 
jacketed mixing vessel of iron — ^provided with means for heating 
and cooling by passing steam or water through the jacket— are 
mixed 22-5 kg. of acetone and 15 kg. of benzaldehyde. The 
mixture is cooled to about 10°, and 8-7 kg. of 10 per cent, caustic 
soda solution are slowly added with vigorous stirring. The 
solution becomes lemon yellow in colour. As a result of the 



reaction, 2-54 kg. of water. are produced, and, in order to maintain 
the strength of the solution, ten hourly additions of 250 grams of 
20 per cent, caustic soda solution are made, and the mixture is set 
aside for two days. At the end of this period 20 kg. of cold water 
are added, thus causing the benzylidene-acetone to precipitate as 
a brown oU. After wasliing with dilute acetic acid and sodium 
carbonate solution, the oil iS distilled under diminished pressure, 
a bright yellow oil coming over at 151° to 153° under 25 mm. 
Tliis oil possesses a fresh and characteristic odour, and after a 
short period, especially if sown with a crystal, the oil solidifies 
to a bright yellow crystalline solid melting at 41° to 42° C. 

On account of its exceptionally penetrating nature, benzylidene 
acetone should be used in perfumery with great caution, and only 
as a 10 per cent, solution in alcohol. Its stabfiity to allvali makes 
it of special value as a soap perfume. In its concentrated state 
benzylidene acetone violentlj’- attacks the skin. M.D. 

BERGAMIOL. — This is a name often used for so-called 
artificial bergamot oil, consisting principally of linalyl acetate 
made from linalol obtained from linaloc or other oils. 

BERGAMOT OIL. — This oil is one of exceedingly soft and 
sweet odour, and is indispensable m the manufacture of many 
perfumes. It finds a prominent place in all formulaj for eau de 
Cologne, in many for lavender water, and in a very large number 
of other fancy perfumes. It is expressed from the peel of the fruit 
of Citrus a^irantnm, sub-species Bergamia, a tree belonging to the 
natural order Rutacece. The chief centre of the bergamot industr}^ 
is southern Calabria, in which district practically the whole of the 
supply of bergamot oil is produced. There are extensive planta- 
tions in the neighbourhoods of Reggio, Melito, Gallico, S. Lorenzo, 
and other districts. The oil is expressed by machines, distilled 
oil losing much of its odour and being of little value to the 
perfumer. The oil varies in colour from a rich golden brown to 
a distinct green, usually the latter. The green colour is due to 
the presence of traces of chlorophyll, and not, as is often stated, 
to copper. The fruits are gathered during November and 
December, and the oil expressed from the peel and packed in 
coppers or tins for exportation. 

Pure oil of bergamot has the following characters : specific 
gravity, from 0-880 to 0-887 ; optical rotation, -f 8° to 22° (rarely, 
a little higher) ; and refractive index, 1-4640 to 1-4675. It should 
yield from 4-5 to 6-5 per cent, of solid residue when dried 


on a 


^Ta^er bath. This consists of wax, colouring matter, and other 
substances dissolved by the oil from the peel, including bergaptene 
{q.v.). The jirincipal odorous constituent is linatyl acetate, 
CjoHjy.CO.T.CHT, which is present to the extent of about 38 to 
42 per cent. Oils with much less than 38 per eent. are usualty 
adulterated, the principal adulterant in such cases being lemon 
terpencs. Such adulterated oils are often fortified with artificial 
esters to bring up the ester value, in the hope that they will be 
regarded b,y the user as natural esters. The presence of many 
such artificial esters is revealed b}" the increase in the weight of 
the non-volatile residue, and bj^ the high saponification value of 
the latter. The normal residue on the water bath has an acid 
value about 18 to 30, and an ester value of llo to 180. 

If unripe fruits are used for the preparation of the oil, it may 
have a sj^ecific gravity domi to 0-S7S or 0-879, and contain less 
than 30 per cent, of esters. 

During the iwcsent season (1923-1924) the writer has found 
undoubtedly authentic samples of bergamot oil having cpiite 
abnormal characters. The oils contained only about 35 per cent, 
of esters, had a low siDccific gravity — ^from 0-880 to 0-881 — and 
contained between G and 7 per eent. of fixed residue. This fixed 
residue is normal in character. Ogston and Moore (P. ct E. 0. R., 
1924, 78) have also recorded such .samples, which appear to 'be 
due to imperfect ripening of the fruits. 

There is a bastard bergamot, known as bergamotella {Nero de 
Bergamotio), which is occasional^ mixed with the normal fruit. 
In such cases the specific gravity is raised, as the oil from the 
bastard fruit often reaches 0-898, and the ester value is reduced 

Bergamot oil contains, besides linalyl acetate, limonene, pinene, 
camphene, bornylene, bisabolene, Zccro-linalol, dihydrocumic 
alcohol, nerol, terpineol, and bergaptene. 

BERGAPTENE. — This body is the principal constituent of 
the residue of oil of bergamot when evaporated on a water bath. 
It is present to the extent of about 5 per cent. It has the formula 
CjoHgO.!! Eiwd melts at 188°. It is the methyl ether of a phloro- 
glucinol derivative allied to coumarin, and is isomeric vdth 

BETA-IONONE.— See “ lonone.” 



PEl^FU M E li Y 

BETEL, OIL OF. — The essential oil of Piper heth (Chavica 
hetle) is distilled from the leaves of the plant, one of the Piperaceoi, 
Tlie leaves jneld up to 1 per cent, of oil (occasionally higher), vith 
a characteristic odour of the plant. It is a heavy, yelloudsh liquid 
of specific gravity, usually from 1-020 to 1-050, but sometimes 
only about 0-960. Its refractive index is over 1-5000. It contains 
methoxy-chavicol (betel phenol) as its principal constituent, 
together vitli a little chavicol, a sesquiterpene, and possiblj’- cineol 
and cjnnene. Its odour is persistent and typically phenolic. 

BETEL PHENOL. — ^This body is identical with chavibetol, 
the phenolic constituent of betel oil. {Vide “ Chavibetol.”) 

BETULA LENTA, OIL OF. — See “ Birch (Sweet), Oil 

BEU-RIENG, OIL OF. — ^This essential oil is lu-oduced in 
certain districts of China, and is probably the product of either 
an Alpinia or a Zingiber species, but at present its origin is 
uncertain. It has a very pleasant odour, recalling that of an 
infusion of tea. Its specific gravity is 0-902 ; optical rotation, 
— 8° 8' ; and refractive index, 1-4884. It contains over 30 per 
cent, of free alcohols (Gattefosse, La Parfwnerie Moderne, 1922, 

BEURRE DE VIOLETTES, — Owing to its pronounced 
violet odom-, the concrete oil of orris is frequently Imownmnder 
this name. 

BIGARADE. — ^This name is applied to the essential oils 
derived from the bitter orange fiowers and fruits, e.g., “ oil of 
orange bigarade ” and “ oil of neroli bigarade,” in contradistinction 
to the corresponding oils from the sweet orange, which are known 
as “ oil of orange Portugal ” and “ oil of neroli Portugal.” 

BIGNONIA. — Bignonia suaveolens {Sterosperimim snaveo- 
lens) is a plant whose flowers possess a most exquisite fragrance, 
but - so far facilities do not appear to have allowed any practical 
use of them in the perfumery trade. The tree is foiuid tlu’oughout 
the nioister parts of India. It is the Pdtald of Sanskrit vwiters, 
and is kno\vn as Kama-duti (messenger of love) or Madhu-duti 
(messenger of spring). The flowers are very 'beautiful in appear- 
ance, and of exquisite perfume. Bees prefer them to any other- 
flower, and native poets describe them as the quiver of Kamadeva, 
the Indian Cupid (Sir W. Jones, “ Asiatic Researches,” iv., p. 289). 



BIRCH (SWEET), OIL. OF. —The flavotu’ and perfume of 
■uintergreen are very highly appreciated, especially in the United 
States. As a perfume material, however, the essential oil of 
wintergreen is used in this country, not to a great extent for its 
ovn odour to predominate, but in small quantities, to modify 
other and more pronounced odours. But as the essential oil of 
wintergreen is practically identical with the oil distilled from the 
bark of Bciula Icnia, the " sweet birch,” true oil of wintergreen 
is lo-daj' seen but little in commerce, as sweet bkcli oil can be 
obtained at a much lower price. It should therefore be under- 
stood that the expression ” oil of wintergreen ” is usually meant 
to indicate that the product is either the distillate of the winter- 
green leaves {Ganltheria procumhens) or of birch bark {Betula- 
hnia). the price indicating whether it be the former or the 
latter. But it is to be feared that in most cases it is, in fact, 
the distillate of Betula lenia, whatever the price may indicate. 
Both oils, however, consist almost entu’ely of the' ester methyl 
salicylate {q.v.), so that there is a good deal of fraud in the article, 
the cheap artificial ester being very frequently substituted for the 
more expensive natiu’al oil. Apart from price considerations, how- 
ever, there is j)ractically no difference between oil of wintergreen, 
oil of sweet birch, and artificial method sahcylate other than a 
slight difference in the delicacy of the odour, in regard to which 
the individual perfumer must make his own decision. 

The true wintergreen, GauUheria procumleiis, is known also 
under the names mountain tea, box berry, spice beny, and ground 
holly. It is a small creeping slu’ub found in the southern parts 
of Canada and the northern parts of the United States. All parts 
of the plant contain essential oil, but the leaves are almost 
exclusively used for distillation purposes. The apparatus ui^ed 
for distillation is primitive m character, consisting of small 
whiskej’- stills or of wooden casks with copper bottoms. The oil 
does not exist as such in the plant, but in combination as a 
glucoside, gaultherine, which is decomposed on distillation. 

The sweet bu’ch {Betula leuta) is a tree which attains a height 
of 10 to 25 feet, occasionally growing to a height of 76 feet. It 
is found in moist woods from New England westwards to Illinois, 
and thence along the Alleghany regions southwards. The best 
yield of oil is obtained from the wood cut in the summer months. 
The wood is cut into small pieces and allowed to macerate in water ‘ 
for twelve hours before distillation. 

The characters of wintergreen and sweet birch oils are practically 



identical. The specific gravity varies from MSO to MS7, and 
both oils contain from 98-6 to 99-6 per cent, of methyl salicylate. 
Power and Kleber {ScMmmeVs Bepori, October, 1895, 50) have 
made an exhaustive examiuation of the two oils, and their results 
indicate that there are only minute differences between the two 
, oils. It is suggested that oil of wintergreen has a very small 
optical activit}- — not less than — 0° 25', whilst sweet birch oil 
is opticaUj- inactive. This, however, is very doubtful. A sesqui- 
terpene alcohol, betulol, C^sHo^O, and its acetic ester have been 
identified in sweet birch oil. A test for distinguishing between 
the two oils has been suggested bj^- J. C. Umney (P. cO E. 0. B., 
1914, 5, GO). To 5 drops of the oil in a test-tube add 5 drops 
of a 5 per eent. alcoholic solution of vanillin and 1 c.c. of alcohol. 
Shake well, and add 2 c.c. of concentrated sulphuric acid, and mix 
thoroughly. Pure wintergreen oil gives an intense crimson-red 
colour, pure sweet birch oil gives a deep blood-red colour, whilst 
synthetic methyl salicylate gives a yellow colour. 

GaiiliJieria punctata, a plant found in British India and the 
Dutch Indies, yields an essential oil practically identical with the 
oils described above. 

GaultJieria fragrantissima has been experimentally distilled for 
“ wintergreen ” oil in Assam, but the ;ydeld has, so far, not been 
sufficient for it to be a commercial success. 

If the oil is found to contam traces of chlorine (see under 

Benzaldehyde), it is certain that it is, or contains, artificial 
methyl salicjdate. When of good quality, the artificial ester 
should contain at least 99 per cent, of true methyl salicylate. It 
has the following characters: specific gravity, 1-182; optical 
rotation, 0° ; refractive index, 1-5375 ; and boiling point, 224°. 

Artificial cassie oil, new-mown hay, and chypre perfumes 
■-usually contain very small quantities of methyl salicylate. It 
is also largely emploj^ed as a flavour for chewing gum and for 
tooth pastes and powders.' 

DIRGH tar oil. — ^T his oil is used to dress certain types of 
leather, originally for the purpose of covering objectionable odour, 
but to-day rather to impart to the leather the pleasant odour 
known as that of “ Russia leather.” It is prepared in Russia by 
the destructive distillation of the wood and bark of Betula alba. 
The crude tar is redistilled and a brownish oil is obtained, which 
is known as rectified birch tar oil. It is a liquid of specific gravity 
from. 0-920 to 0-946. It contains over 40 per cent, of phenols, 
principally guaiacol, creosol, cresol, and xylenol. The crude oil 


P E P F U iV E F Y 

has a specific gravity 0-928 to 0-9G0. If a. 5 per cent, solution in 
2 octroleuin ether be shaken vitli a 0-1 per cent, aqueous solution 
of cojqDer acetate, it should not become green in colour (absence 
of fir tar as an adulterant). This oil is known in pharmac}’’ as 
OJewn Evsei. 

BISABOL MYRRH. — See under “ Myrrh ” and “ Opox^onax." 

BISABOLENE. — This body is a sesquiterpene, C 15 H 04 , found 
in the essential oil of bisabol myrrh. It is identical v'itli the 
hydrocarbon originally discovered in oil of limes by H. E. Burgess, 
and named by him limene. It is a colourless oil having a .specific 
gravity 0-SSl ; optical rotation, — 41° ; refractive index, 1-4901 ; 
and boiling at 112 ° at 4 mm. jiressure. It has an odour of myrrh. 

BITTER ALMOND OIL. — See “ Almonds, Oil of.'’ 

BITTER ORANGE OIL.— See “ Orange, Oil of.” 

BLE DES PAGODES.— The essential oil known under this 
name is of unknown botanical origin. It emanates from Annam, 
and lias been investigated by Roure-Berlrand Fils [Bulletin, April, 
1920, 32). It resembles in odour the oils of palmarosa and ginger- 
grass, with a definite odour of cummin. 

BLUMEA, OILS OF. — The oil from Blumea halsamifera is 
an aromatic liquid containing Zccro-borncol, Zcero-camiDhor, a 
sesquiterpene, a sesquiterpene alcohol, cineol, limonene, and about 
5 per cent, of a ifiienolic compound. It has been examined by 
Jonas [Schimmel <0 Co., Bericlit, April, 1909, 149), who found it 
to have the following characters : — 

Specific gravity . . . 0-950 

OiDtical rotation . . . . — 12° 30' 

Refractive index . . . 1-4815 

Acid value .... 23-4 

Ester value .... 1 

Ester value after acetylation . 198 

The phenolic compound is probably iDliloroglucinol-trimethyl 

Blumea halsamifera is indigenous to India, and is found from 
the Himalayas to Singapore, and in the Malay archipelago. It is 
also found in the islands Hai-nan and Formosa. In Hai-nan and 
IXAvang-tung it is distilled for the production of Ngai camphor, 
as it is called, or Nga'i-fen, as the Chinese caU it. This substance 
is used for ritualistic purposes, and also for the manufacture of 
' 96 


so-called “ Chinese inlc,” and in medicine. Ngai camphor is the 
loevorotatory variety of borneol, 

Simonsen and Ran {Jour. GJiem. Soc., 1922, 876) have examined 
the essential oil of Bhmca Malcomii. This is a small herb, known 
in Marathi as Panjnil. It occurs in the western part of the Deccan 
plateau at elevations of about 2,000 feet. It has a pleasant 
camphoraceous odour. The fresh green material yielded about 
0'2o per cent, of essential oil, which was found to consist almost 
entirely of two ketones, d-carvotanacetone and Z-tetrahj^dro- 
carvone. Traces of acids, esters, and a phenol were found. 

BOG MYRTLE.— The bog mjTtlc (sweet gale, bastard 
myrtle), Myrica gale, has no connection with the true mjTtle. 
It is a native of Britain, and is found in France, Holland, northern 
Europe, and the United States. It is a small fragrant shrub, 
found chiefly in boggy places. Its leaves yield a small quantity 
of a fragrant essential oil having a specifle gravity from 0'89S to 
0-915 ; optical rotation, — 5° to — 12° ; and ester value, 15 to 
25. The principal odour value of the plant, however, lies in the 
fact that the fruit consists of a very large quantity of small berries, 
which jdeld, on treatment wth hot water, a quantity of wax 
which, when used for candle manufacture, gives off a delightful 
odour on burning, hlyrtle wax is somewhat variable in colour, 
usually of a yellowish green shade. 

BOIS DE CITRON.— See under “Bois de Rose” and 
“ Linaloe Oil.” 

BOIS DE ROSE, OIL OF.— The so-called oil of Bols 
Rose must not bo confounded with oil of rosewood {q.v.), which is, 
as found in commerce, usually an entirely factitious oil. Oil of 
Bois de-Rosc is frequently known as cayenne linaloe oil, and here 
again must be distinguished from hlexican linaloe oil, which is 
the product of various bursera species. Cayenne linaloe oil, or 
oil of Bois de Rose femelle, as it is described in full, has usually 
been described as the product of a tree known as Licari Kanali. 
The botanical origin of the oil has, however, been very obscure 
until B. M. Holmes published the most reliable account of the 
matter in 1910 (P. & E. 0. R., 1910, 32). The wood, he states, 
has been named by various writers Bois de Citron, Bois de Rose 
male, Bois de Rose femelle, Bois de Cedre jaune, etc. According 
to Guibort, the name Bois de Citron has been applied to three 
distinct woods, namely : (1) that of Amyris balsamifera, now 
known to be the tree yielding the West Indian so-oalled sandal- 
P. W f 

P E P F U M E R Y 

wood oil ; (2) an miknonTi wood of weak odour ; and (3) Bois de 
Giiron de Cayenne, also sold as cayenne sassafras wood. TMs is 
the wood which yields cayenne linaloe oil. It is the product of a 
tree for which the native Indian name is Licari Kanali, and is 
known the French inhabitants as Bois de Rose male. The 
wood known to the French inliabitants as Bois de Rose femelle 
appears to be the product of Protium altissimum [Idea altissima). 
This has a lemon-bergamot odour, and differs entirely from Bois 
de Rose male. 

So that what is known in Europe as oil of Bois de Rose femelle 
is, in fact, derived from Bois de Rose male, the oil from the Bois 
de Rose femelle not being a commercial article at all. Aublet 
named the tree Licari guianensis (“ Plantes de Guiane Frangaise,” 
p. 313), but, after fuller investigations. Dr. Moeller showed that 
there vms little doubt that the tree was Ocotea candata. It may 
be therefore taken for granted that oil of Bois de Rose femelle, 
or ca 3 'enne linaloe oil, is the product of the wood of Ocotea caiidaia, 
known in Guiana as Bois de Rose male. The oil obtained by the 
distillation of the wood is a colourless or pale j'^eUow oil of soft, 
sweet odour, in which that of its principal constituent, hnalol, 
predominates. It is used for the manufacture of linalyl acetate, 
the basis of artificial bergamot oil, and as a constituent of such 
perfumes as lily of the valley, hawthorn, honeysuckle, jonquil, and 

The pm’e essential oil usually has the following characters : 
specific gravity, from 0-870 to 0-882 ; optical rotation from — 9° 
to — 18° ; and refractive index, 1-4600 to 1-4640. It contains 
only a very small quantity of esters, but from 60 to 80 per cent., 
sometimes even 90 per cent., of free hnalol. It is soluble in 
2 volumes of 70 per cent, alcohol. In determining the total 
alcohols in the oil, as in aU oils containing much linalol, special 
precautions must be taken, or the linalol will be decomposed in 
the process. To acetylate the oil it should be dissolved in four 
times its volume of xjdene and boiled for about five hours. 
[Vide “ Alcohols, Determination of.”) 

Messrs. Chins & Co_. [Les Parfums de France, 1924, 13, 50) 
have found that many genuine, samples of this oil distilled by 
themselves have specific gravities up to 0-886. They consider 
that acetylation in xylene solution gives too low results, and 
that formylation for eighty-four hours in the cold (about 25°) 
and saponification for ninety minutes give the, most accurate 
determination of the hnalol present. 



A terpeneless oil of Bois tie Bose is sometimes offered as being 
higlil.y concentrated. When it is remembered that the natural 
oil contains 60 to 90 per cent, of the active constituent, it is 
obvious that there is not much room for concentration, so tliat 
in this case the terpeneless oil possesses but little advantage over 
the natural oil. 

In addition to linalol, the oil contams gcraniol, terpineol, cineol, 
dipcntenc, traces of furfurol, mcth 3 *l-heptenone, nerol, and 
probablj' isovaleric aldch 3 "de. Bonre-Berlrand Fils {Bulletin, 
October, 1909, 40) give the following as the composition of the 
oil : — 

j\Ieth 3 'l-licptcnone 
i/ccro-linalol . 
Gcraniol . 


Other bodies . 

90-5 per cent. 

0 - .3 

1 - 2 

BOKHARA GLOVER.— This plant, 3Ielilotiis alba, is a 
favourite vdth bees on account of the nectar present in the white 
clover blossoms. It is one of the conti'ibutoiy causes of the 
perfume of new-movm ha 3 ’', a perfume which is to some extent 
imitated b 3 r using coumarin as the basic material. 

BORNEO CAMPHOR. — ^This name is the common name for 
tZc.'Clro-borneol. It is also termed Baros camphor, Mala 3 ’' camphor, 
and Sumatra camphor. (Vide ” Borneol.”) 

BORNEO CAMPHOR OIL.— The wood of Dnjobalanojis 
aromalica, the so-caUed Borneo camphor tree, 3 delds this odorous 
essential oil, which contains de.rZro-borneol. It is not often seen 
in commerce, and is a colomless or pale 3 'ellow oil of specific 
gravity 0'918 ; optical rotation, + 11° ; and refractive index, 
1-4885. It contains pinene, camphene, d-borneol, dipentene, 
terpineol, and sesquiterpenes. 

BORNEOL. — ^Borneol CioHj^OH is the alcohol corresponding 
to the ketone camphor. It occurs naturall 3 ^ as de.rZro-borneol in 
Dryobalanops campUora, and as Zcct’o-borneol in Blumsa balsamifera. 
It forms crystalline masses or fine needle-like crystals, which melt 
at 204° and boil at 212°. Numerous oils of pine needles, derived 
from Abies and Pvnis species, contain both free borneol and 
bornyl esters. It is also produced artificially by reducing camphor 
with sodium. Borneol forms a well-defined series of esters with 
organic acids of which bornyl acetate is the principal, and rvhich 

99 ' 7—2 


lias a fine pine needle odour. Tlie following method may he used 
for distinguishing between borneol and isoborneol. The alcohol 
to be tested is dissolved in about ten times its weight of pyridine, 
and the calculated quantity of ^a?'o-nitrobonzoyl chloride added, 
and the mixture heated on a vaater bath for several hours. The 
J)'^Tidine is removed 113 ^^ extracting with ice-cold dilute sulphuric 
acid, and the paw-nitrobenzoate of the alcohol is separated, dried, 
and 'recrystallised from alcohol. The borneol compound melts 
at 137°, whilst the isoborneol compound melts at 129°. 

BORNYL ACETATE. — ^Borneol itself occurs in the free 
state to a large extent in certain pine needle oils, spike lavender 
oil, etc. Its acetic ester, born 3 d acetate, C 10 H 17 .O 0 C.CH 3 , is found 
in certain pine needle and other oils, and is a substance of ver 3 ’' 
refreshing odour, recalhng that of a pine forest. It is manufactured 
artificial!}’' by the esterification of borneol by acetic anh 3 ’'di‘ide, 
and, when pure, is a ciystalline solid melting at 29°, of specific 
gravity about 0-990. Its refractive index is 1-4645 at 15°, and 
boiling point 9 S° at 10 mm. pressure. When liquefied, it often 
remains liquid without solidif 3 dng for a considerable period. The 
commercial article is a mixture of born 3 d and isoborn}’’! acetates, 
having an optical rotation about -f- 20 °. 

BORNYL BUTYRATE. — This ester, of the formula 
C 10 H 17 O 0 C.C 3 H 7 , is very similar to the acetic ester, but is rather 
more camphoraceous in odour. It is a liquid boiling at 121 ° at 
10 mm., and having a specific gravit}’' 0-996 ; optical rotation, 
-|- 22° ; and refractive index, 1-4638 at 15°. 

BORNYL FORMATE.— This ester, O 10 H 17 OOCH, is manu- 
factured artificially, and is a liquid of specific gravity 1-013 ; 
refractive index, 1-4708 ; and boiling point, 90° at 10 mm. 
pressm’e. It has a refreshing pine odom’, and is useful for blending 
with borneol and all its esters. The commercial article is a 
mixture of bornyl and isoborn 5 d formates, having an optical 
rotation about — 47°. 

BORNYL PROPIONATE.— Although obtainable commer- 
cially, this ester, C 10 H 17 .O 2 C.C 2 H 5 , is not often used in perfumery, 
as it does not differ very materially in odour from the butyrate. 
It is a liquid of specific gravity 0-978 ; optical rotation, -j- 24° ; 
and refractive index, 1-4643. It boils at 110 ° at 10 mm. 

BORNYL VALERIANATE.— No higher ester of borneol is 
manufactured than this body, which actually is principally the 



isovalerianate of the formula CioHi^OgC.C^Hg. It is a liquid 
having a specific gravity about 0-956 ; optical rotation, -{- 15° 
to + 20° ; refractive index, 1-4628 ; and boiling point, 130° at 
10 mm. It has a rather more fruity odour than the lower esters 
of borneol. 

BORONIA, OILS OF . — Boronia ihujona is a tall shrub 
growing in Xew South Wales. The leaves and terminal branchlets 
yield about 0-5 per cent, of an essential oil which is coloiu-less, 
with a slight fluorescence, and an exquisite odour of black currants. 
It has a specific gra\dty 0-912 to 0-915 ; optical rotation, + 13° 
to ■— 56° ; and refi-active index, 1-4524 to 1-4569. It contains 
80 to 90 per cent, of thujone, thiijol, esters, a sesquiterpene, and 
a paraffin hydrocarbon. H. G. Smith {Proc. Roy. Soc. Victoria, 
1919, 32, i.) has examined the oil from Boronia 'pinnaia, which 
has a rose-geranium odour. It has the following characters ; — 

Specific gravity at 15° . 

Optical rotation ..... 
Refractive index at 20° .... 

Saponification number (on heating) . 
Saponification number (in the cold) . 
Geranyl acetate ..... 
Saponification number on heating, after 
acetylation . . . . . 

Saponification number after acetylation in 
the cold ...... 

+ 3° 8' 

6-4 per cent. 

According to the author, the oil of Boronia pinnata contains 
free and combined geraniol as acetate and butyrate, trimethyl- 
gallic acid, and 70 per cent, of elemicine. 

BOSWELLIA RESIN. — ^Tliis important gum resin, known-as 
olibanum or franlcincense, is of considerable value to the perfumer, 
and is used, as its common name would imply, in the manufacture 
of incense. The name olibanum is to some extent of common 
origin with that of gum benjamin {q.v.). It is derived from the 
Hebrew word Ichonali, meaning milk, through the Arab Luhan, 
meaning incense, and was known to the Greeks as Libanos, and 
to the Romans as Olibanum. E. M. Holmes (P. & E. 0. R., 1916, 
79), in a paper dealing exhaustively vdth this substance, quotes 
the following method of trading between the natives who collect 
gold and the traders, who do not understand each other’s . 
languages. ” The gold caravan, which consists of some 500 traders, 
arrives in the highlands of Abyssinia, and brings with it salt 








and iron and cattle, and set up a hedge against which they place 
joints of meat, salt and iron, and then retire. - The natives then 
ap])roach, and each places what gold he considers adequate on 
what ho fancies. They, too, then retire. The traders then return 
and inspect wdiat has been offered. If content, they remove the 
gold and leave the goods in exchange ; otherwise, they again 
retire and leave the natives to again approach. This they do, and 
either place more gold on the goods or take wdiat they’ had 
previously left, if they do not consider the goods of an}'- higher 
value.” The collection of frankincense in the early days appears 
to have been carried out on a similar basis. Aecording to Holmes 
(Zoc. ni.), the libanotophoros or frankincense -}delding region of 
the old Sahseans in Arabia wns visited by Carter in 1844-1846, and 
is stated by him to extend on the southern coast from 52° 47' to 
58° 28' E. longitude, and a frankincense tree found there w'as 
described and illustrated by him in the Journal of the Bombay 
Branch of the Royal Asiatic Society, vol. 11, tab. 23, and subse- 
quently named after him as Bosivellia Carleri by Dr. (now Sir G ) 

Whether the ancient Sabaians derived any portion of frank- 
uicense from the opposite coast of Africa, now known as Somali- 
land, is uncertain, although they w’ere in the time of Solomon 
(1000 B.c.) in constant communication with the natives of that 
region, but that it did produce olibanum wns midoubtedly known 
to the Homans in the time of Strabo and Ai’rian of Alexandra, 
since the latter (a.d. 54r-68) states in the “ Periplus of the 
Erytlu’fean Sea ” that olibanum wns exported thence, partly to 
Eg}q3t and partly to Barbaricon, at the mouth of the Indus. At 
that period the whole of the coast of modern Somaliland from 
Zeyla (then called Aulites) to Cape Gardafui (then called Promon- 
tarius Aromaium) wvas known as Barbarica, and the eastern 
portion of it as Regio Cinnamomifera, w'here cinnamon Wns 
supposed to be produced, since the Romans imported it from the 
port of Mosyllum on that coast. This should not be surprising, 
since in modern times m}nrh wns ealled “ Turkey myrrh,” and 
rhubarb “Turkey and East Indian rhubarb,” long after their 
geographical scurce was known, and, similarly, Goa pow'der is 
now known not to be produced at Goa in India, but in Brazil. 
It seems probable, though it is not certain, that during the Roman 
occupation of Egypt the trade in frankmcense, which w'as 
previously centred in Moscha, near Bhofar, the ancient emporium 
on the south Arabian coast, may have been diverted to Mosyllum, 



a port on the opposite African coast, which was in the very centre 
of the African frankincense-bearing region. 

Tile authors of “ Pharmacographia ” (1879) state that, at that 
date, the ohbanum of Arabia was shipped, from several small 
places on the Arabian coast between Damkote and A1 Kammar, 
but the quantity produced in this district is much below that 
furnished by the Somali country in Eastern Africa.” The Somali 
franlcincense is sliipped from Bunder Murrayah, Berbera, and 
many smaller ports to Aden, or direct to Bombay. The trade is 
eliiefly in the hands of the Banians, and the great emporium of 
the ^ug is Bombay, but a certain portion is shipped through the 
Straits of Bab-el-Mandeb to Jiddah, according to Von Kremer, 
to the value of £12,000 annually. 

It does not seem clear from the context whether the native 
Arabs still collect franlcincense in southern Arabia, since the 
authors quote the statement of Captain Mes (Joicr. Roy. Geog. 
Soc., 1872, vol. xxii., p. 65} that the drug is not collected by the 
people of the country, but by Somalis, who cross over in numbers 
to the Arabian coast, pa 3 dng the Arab tribes for the privilege, and, 
further, that it would even appear that the names of Luhan Maher i, 
or Mascati, or Sheehaz, referring to places on the coast of Arabia 
between 52° 10' and 54° 32' E. longitude, are now apphed to 
olibanum brought from the opposite African coast. The authors 
also state that “ Hddebrandt informed one of us (December, 1878) 
that he has ascertained at Aden that all the franlcincense imported 
into Aden comes from Africa.” 

The latter statement does not quite agree with that of Vaughan, 
who in 1853, in a paper on “ The Drugs observed at Aden ’’ 
(communicated by D. Hanbmy to the Pharm. Jour. (1), xii., 
p. 229), states that a large quantity of olibanum is collected in 
the southern and south-eastern districts -of Ai-abia and exported 
from several towns on the coast between Has Eartak and Marbat, 
the famous thuriferous region which proved the object of such 
diligent search in ancient times. 

Vaughan also describes several commercial sorts of African 
frankincense occurring in the Aden bazaar, and there known by 
the names of Luhan Mattee, Zniban Malcur, and Luhan Berber a 
or Mustika, named after the ports from which they are exported 
to Aden. The most important of- these are : (1) lAihan Berhera, 
which is coUected by the Ayil Yunis and Ayil Hamed tribes in 
the west of Somaliland and brought in to Berbera ; (2) Luhan 
Hunkur or Aungure, coUected by the Dour Mohammed and 



Abarclagaliala tribes in central Somaliland and brought to the 
port of Aungure ; (3) the Lvban Maknr, which is collected in the 
east of Somaliland by the Worsungali and Meggertein Somalis in 
May, June and Julj^ and carried to the neighbouring ports, such 
as Bunder Koor and Bunder Kassooin, and is nearly all taken 
across to Maculla and Shehr, on the Arabian coast. This possibly 
comes back to Aden as the Lvhan tShoharrec or Liihan Morhat, 
supposed by Vaughan to be produced in Ai’abia. 

The L'liban Ilaflce described by Vaughan is collected chiefly 
b}^ the Abardagahala tribe in central Somaliland and brought to 
the port of Llaiti, near to the ancient Mos3dlum, for export, whence 
the name of Liihan Maili or Maycti. 

Vaughan also distinetty affirms that three baggalas were annual^ 
freighted from ]\Iarbat to Bombaj’' with an enthc cargo of the 
Arabian frankincense, which realises a higher price in the market 
than an}’ of the qualities exported from Africa. The onlj^ jDrobable 
explanation of these contradictory statements is that frankincense 
is collected in Arabia b}’ Somalis and exported dhect to Bomba}'', 
and that some of it is sent back from Bombay to Aden cn route 
for Eurojoe. 

The latest account of the frankincense region of Somaliland is 
given by Dr. E. Drakc-Brockman, E.B-.G.S., in “ British Soinah- 
land ” (1914). He states that the drug is produced in the coast 
regions, more especially those occupied by the Habr Toljaala, 
Warsangah, and Mijcrtain tribes, and that the di’ug is known to 
the Somalis as Beyo or Hanjibeyo ; also that there arc two distinct 
varieties, ealled by the Arabians Loban Dakar and Loban Ilaidi, 
i.e., male and female frairkincense respectively. The tree yielding 
Loban Dakar is called by the Somalis IloJior or Molmr, and is 
Boswellia Carferi, wliilst the tree yielding Loban MakJa is called 
Ycliar, and is BosicelUa-Frcreana, 

The former is found on the maritime limestone mountainb 
eight miles south of Berbera in western Somaliland, and thence 
eastwards, whilst BosiccUia Frereana is not found until the Habr 
Toljaala country is reached, and extends further west into the 
country of the Warsangali and Mrjertain tribes. 

B. Carieri was first described by Speke as a tree with rugged 
bark and smooth epidermis of a reddish tinge, pleasant aromatic 
odour, and strong astringent flavom’, and as used for tanning 
skins. Powdered and sprinkled dry on a wound, it acted as a 
styptic. Dr. Drake-Brockman describes- the freshly collected 
drug as follows : Both the varieties are found in small tears, and 



are mixed up with bark, sand, and other foreign matters, and 
have to be sorted, which is usually done at Aden, the picked 
samples of Loban Dakar being sent to Europe, whilst the Eoba^ 
Maidi is sent to India and Egypt. The inferior qualities of each 
are done up separately in sacks of matting and sliipped back to 
Africa most of it finding its way to Abyssinia. The Loban Dakar 
is shipped from Aden to London and Hamburg, where it is made 
into false amber beads, which are threaded into necklaces and 
rosaries, much w^om by the Arab and Somali wmruen. The tears 
of the two kinds are not difficult to distinguish, the tears of Loban 
Dakar beiug usually darker and of a more amber colour ; the tears 
of Loban Maidi are paler and clear like a topaz. The latter, when 
packed, generally becomes formed into large masses, whilst the 
Loban Dakar, being drier and more friable, does not usually con- 
glomerate so readily, and does not form so plastic a mass when 
chewed. In the form of emulsion, it is sometimes given for venereal 
complaints. The Loban Maidi is chewed by the Somalis, and is 
sometimes used in the chewed state as a cement. A variety of 
Loban Maidi is sometimes found in large stalactitic pieces formed 
by the oozing and trickling down of the milky juice. These pieces 
may be 6 inches or more long and 3 or 4 broad, and present a 
characteristic appearance, having an irregular surface with many 
small protuberances and being covered with white powdery 
streaks, and, when fractured, showing alternate white and clear 
layers, and on the under surface often have pieces of the papery 
outer bark attached. 

The colour varies in both kinds, being often pale in the Loban 
Dakar and deep orange in the Loban Maidi. The Loban Dakar 
is sometimes found in pieces the size of a hen’s egg, but is then 
invariably composed of small agglomerated tears. 

As regards the name Beyo and Hanji-beyo, Dr. Drake-Brockman 
explains that the prefix Hanji is applied to any gum resin that is 
used for chewing. It therefore applies more strictly to the 
Loban Maidi, which is used for that purpose. 

In- Bombay frankincense passes through the Custom House 
under the name of Es^ {Isas of Drake-Brockman), and is there 
sorted into four or five different qualities, the first, consisting of 
large clear tears, being destined for the European market. The 
intermediate qualities, as well as the last, knoAvn by the Indian 
name of Dhup, consisting of pieces of the bark coated with 
frankincense, supply the Indian or Chinese market. 

The Mahometan writers describe five kinds under the Sanscrit 


P E R F U 3{ ERY 

name of Knndnr, as follows : (1) Kundur Zahar, or male frank- 
ineense, in deep yellow tears ; (2) Kundur Unsa, or female 

frankincense ; (3) Kundur lladahroj, artificial tears made by 

shaking the moist exudation in a basket ; (4) K^indur Kisliar, or 
Kaslifar, consisting of pieces of bark covered with the exudation, 
identical with the Dhuj:) already mentioned ; (5) Kxmdur Duhak, 
or dust of olibanum. In the London market there are three 
principal forms recognised : ordinary, consisting of irregular or 
more or less oval or pyriform tears, and garblings and siftings. The 
fine large tears known at Aden as Liiban Fasons Bedoiv come from 
the ]\Iijertain district, in the east of Somaliland. The Liiban 3'Iaidi 
of Drake-Brockman comes from the same district, but is not a 
regular article of importation into this countr3^ A very fine 
specimen of it exists in the museum of the Pharmaceutical Society 
at Bloomsbiuy Square, presented some 3"ears ago b3’- Mons. Cesar 
Chantre, a French silk merchant, then residing in London, a 
native of L3mns, who made a hobb3' of the stud3^ of the London 
drug market, and acquii’ed a fine collection, which he subsequenth^ 
presented to Dr. Cauvet, a professor of materia medica in his 
native cit3% who published a few 3’-ears afterwards a little known, 
but most concise, reliable, and almost enc3J'clops3dic work on 
materia medica. 

Until the middle of the last centuiy but little v^as known to 
botanists concerning the trees that 3deld the ohbanum of com- 
merce. In 1846 Dr. J. Forbes Royle suggested, in an article in the 
Pharmaceutical Journal, vol. v., j). 543, that African olibanum was 
probably the produce of a species of Bosivellia of the natural order 
Burseracecc. It was only in 1870 that Dr. (now Sir G.) Buxlwood 
was able to describe as sources of olibanum, Bosivellia Gartcri, 
obtained b5’' H. J. Carter in 1848 on the south-east coast of Ai’abia ; 
Bosivellia Bhau-Dajiana, obtained b3’- Colonel Pla3dair ; and 
Bosivellia, Frereana, from eastern Somaliland, the last-named being 
the soiu’ce of the rarer fiankincense knovm b3^ the Arab name of 
Luhan Ilaidi, Ilaitee, or Ilaiyeti. The species are not the onty 
ones that 3deld frankmcense, since there are several others men- 
tioned in “ Pharmacographia ” from which it is collected, but it 
is doubtful whether the3^ are species or only forms growmg under 
different conditions, some of them occurring on limestone hills 
and valleys in the neighbourhood of the sea, sometimes in lime- 
stone detritus, and others growing out of the rocks on the high 
and precipitous mountain ranges further inland. 

One of those referred to, B. Garteri, is called b3'- the natives 3Iohr 



Meddii- or Madow, i.e., black molir tree, and another referred to, 
B. Frcreana, is called Mahor in Sennaar. Dr. Malcolmson describes 
one of these as growing at about 1 ,000 feet on the hills near Bunder 
Marraj'ah (11° 43' N. latitude) to a height or40 feet, firmly attached 
to the bare limestone by a mass of vegetable substance, part of 
the tree, ■which sends roots into the cre'vices of the rock to an 
immense depth. 

-The trees have jmmate leaves recalling in appearance those of 
the mountain ash, but hany, the branches having panicles of small 
fragrant greenish flowers. The whole plant contains the fragrant 
gum resin, which exudes even from the flowers, when injured, as 
a miUiy juice. The collection of the frankincense is described by 
Cruttenden, who -visited the Somali country near Bunder Mun- 
ra}^!! in 1843, as follows : “ About the end of February or the 
beginning of March, dming the hot season, the Bedouins visit all 
the trees in succession and make a deep incision in each, peeling 
off a narrow strip of bark for about 5 inches below the wound. 
This is left for a month, when a fresh incision is made in the same 
place, but deeper. A third month elapses, and the operation is 
again repeated, after which the gum is supposed to have attained 
a proper degree of consistency. The mountain sides are immedi- 
ately covered with parties of meji and boys, wdio scrape off the 
large clear globules into a basket, wlulst the inferior quality that 
has run dowm the tree is packed separately. The gum, when first 
taken from the tree, is soft, but hardens rapidl3^ Every fortnight 
the mountains are visited in this manner, the trees producing 
larger quantities as the season advances, until the middle of 
September, when the first shower of rain puts a close to the 
gathermg for that year.” 

The collection of the di’ug in southern Arabia is described by 
Carter as follows ; “ The gum is procm-ed by making longitudinal 
incisions through the bark in the months of May and December, 
when the cuticle glistens with intumescence from the distended 
state of the part beneath. On its first appearance the gum comes 
forth white as millc, and, according to the degree of fluidity, finds 
its w^ay to the ground, or concretes on the 'branch near the place 
from which it first issued, whence it is collected by the men 
and boys employed to look after the.trees by the different families 
wFo possess the land in which they gi’ow.” 

Hildebrandt, speaking of the collection of Luhan Meithi, Maiti, 
or Maidi, near Lasgori, in Somaliland, from the Gekar (Yegaar) 
trees, states that the thick, low trunlt of the tree grows out of the 



nearly perpendicular rock, and that the flowers were just blossom- 
ing on March 25th. The Somali men and women reach the trees 
by very dangerous ijaths, and make incisions, and after only six 
days collect the resin. The L^iban Haiti does not contain gum, 
but only oil and resin, and therefore probably dries more quickty 
than the ordinary frankincense. He remarks that it is sold at 
Aden and Geddah (Djedda), and thence finds its way as a masti- 
catory to the harems, and is also chewed bj'’ the Somalis when 
they are tired. 

It is noteworthj'- that it does not seem to have been utilised for 
this purpose, for which its pleasant odour and possibly antiseptic 
properties should render it useful. 

Pure olibanum has, according to Kremcl, the following 
characters : — 




Percentage of resin 




Acid value of resin 




Ester value of resin 




iSaponification value of resin . 


87-8 ' 


Sample No. 1, however, is probabty quite abnormal. 

Olibanum contains a small amount of essential oil, var 3 ’ing from 
5 to 10 per cent., which is a pale j’^ellow liquid of balsamic odour, 
having a specific gravity 0-87o to 0-894 ; optical rotation, -j- 15° 
to + 30° ; and refractive index, 1-4725 to 1-4825. It contains 
a-pinene, camphene, dipentene, para-cymane, and an alcohol of 
the formula CioHjgO which has been named olibanol. Borneol 
esters are present in traces. 

Boswellia sonata is a native of north-west India, and jdelds a 
somewhat similar resin. Apparentlj^ there are two well-recognised 
varieties, the foliola ovato-oblonga and the foliola lineari-lanceo- 
lata. The resin is collected in the Punjab twice a j^’ear. It is 
used for medicinal pm'poses, and is also burned as incense in 
rehgious ceremonials. Experiments have been carried out recentty 
at the Forest Research Institute at Delna Dun vith a view to 
determining the most advantageous method of treating the crude 
gum resin in order to separate the essential oil, the purified resin, 
and the gum. The crude gum resin is placed in a still vdth a 
perforated false bottom, and steam is passed through the mass. 
Most of the resin and oil passes through, and collects at the bottom 



of the still, whilst the gum and impurities remain on the false 
bottom. The oil is then separated from the resin by steam 
distillation, and the oil so obtained is rectified, and then consists 
of almost pure pinene. From experiments on this oil carried out 
at the Imperial Institute it was found that this oil dissolves 
varnish resins, such as dammar, sandarac and soft copal, and 
varnishes prepai’cd vdth it dried with a less lustrous surface, but 
more rapidly, than those made with ordinary turpentine. 

Tinctures of olibanum are used as fixatives, and also in the 
preparation of heavy Oriental odours. Peiiumes containing 
champaca and perfumes of the broom type are improved by 
traces of olibanum, Olibanum is sometimes IcnoA^m as gum Thus. 
(See also under “ Incense.”) 

BOUVARDIA.— This is a fancy name, of considerable popu- 
larity, for a perfume somewhat resembling jasmin in type. It 
is based on such synthetic perfumes as benzyl acetate, hydroxy- 
citronellal and phenjd-ethyl acetate. 

BRILLIANTINES.— These are merely mixtures of perfume 
and oil used as di’essings for the hair. They are usually mixtures 
of an alcoholic solution of perfume with olive, almond, castor or 
petroleum oils, wliich require shaking before \ise, or are simply 
these or similar oils to which a trace of absolute perfumes, free 
from alcohol, has been added, thus forming a one-solution 

known in Queensland as the Avhite sassafras is a species of 
cinnamon, Cinnamomiim oJiveri. The bark yields an essential 
oil of specific gravity 1-030, and refractive index 1-5165 at 23°. 
It contains about 12 to 15 per cent, of pinene, IS to 20 per cent, 
of camj)hor, 25 to 27 per cent, of safrol, and 40 to 45 per cent, of 
eugenol meth3d ether {Jour. Cheni. Soc., 1916, 751). 

BROMACETAL.— Bromacetal is an important intermediate 
product in the mariufactui’c of phenyl-acetic aldehyde, the well- 
known artificial hyacinth base. It has the formula CHjBr.CH 
(0.C2H5)2, and boils at 82° at a pressure of 28 mm. It results 
by adding, very gradually, 51 c.c. of bromine to 45 grams of 
paraldehyde kept at a temperature of some degrees below freezing 
point. After the crystalline mass has liquefied, 200 c.c. of absolute 
alcohol are added and the mixture allowed to stand for twelve 
hours. Bromacetal is not itself used as such in perfumery. 



BROMELIA. — p - iiaplitliol - nietltyl - ether and p - naphthol- 
eth 5 d ether are Wo well-known artificial perfume materials which 
are kno\vn as nerolin. The former is also known as yara-yara, 
whilst the ethyl ether is knoum as bromelia. These bodies have 
the formula C 10 H 7 O.R, where R is the methyl or ethyl radicle. - 

Both have a pronounced neroli odour, that of the ethyl ether 
being rather the finer, with a suggestion of pmeapple. Yara-yara 
melts at 72°, and bromelia at 37°. They may be prepared by 
heating -/?-naphthol-sodium vith methyl, (ethyl) iodide in methyl 
(ethyl) alcohol. One thousand parts 'of 90 per cent, alcohol 
dissolves about 20 grams of yara-yara, and 40 grams of bromelia. 

BROMOSTYROLENE. — This body, of the formula 
CgHj.CH : CHBr, is a very important synthetic perfume. It is 
used to a very considerable extent (as is also phenyl-acetic 
aldehyde {q.v.) ) as the basis of perfumes of the type of hyacinth, 
narcissus and jonquil. It is employed very extensively in soap 
perfumery. St 3 T:olene, CgHg, yields two series of halogen deriva- 
tives, the cu -derivatives and the a-derivatives. For example, 
co-bromostju'olene is CgHg.CH : CHBr, and a-styrolene is Cgllj. 
CBr : CHo. The a-derivatives are useless for perfumery purposes, 
while the w-compounds are highly odorous. w-Bromostyrolene 
is prepared b}^ treatmg cinnamic acid vdth bromine to saturate 
the double linlcage, and 'a molecule of hj^’drobromic acid is 
abstracted by means of caustic aUcali. Levdnsohn (P. c& E. 0. R., 
1924, 119) gives the folloving method for its manufactiue. 
Bromostjuolene is formed from cinnamic acid according to the 
following equations : — 

(1) CgHg.CH : CH.COOH -f Br^ = CcH5.CHBr.CHBr.COOH 

Cinnamic acid Dibromocinnamic acid 

(2) CcHg.CHBr.CHBr.COOH -b Na.COg = 

Dibromocinnamic acid 

CcHg.CH : CHBr -{- NaBr + COg -f HaHCOg. 


Ten kilograms of cmnamic acid and 40 kg. of ether are placed 
in a mixing vessel, wliich is provided with an exceptionally good 
condenser, having a large cooling surface. A means of injecting 
live steam is also provided. 

Eleven kilograms of bromine (3,670 c.c.) are then slowly 
introduced by means of a dropping funnel during continuous 
stirring and strong cooling of the reflux condenser. When the 
addition of the bromine is complete, the stirring is continued for 
some hours, and the ether distflled off — ^the condenser being 



connected to the still by means of a three-way cock, so as to allow 
this operation 'to be condncted by merely tnming the cock. As 
-soon as the ether has been completely removed, a solution of 
7 kg. of soda ash in 20 kg. of water is added, and the reaction 
mixture steam distUled. The bromostyrol distils over with the 
water and collects on the bottom of the receiver. It is rectified 
under diminished pressure. Boiling point, 98° to 99° at 5 mm. 
Bromostyrol turns brown in daylight, and must be kept in the 

a-BromostjTolene, CgHgCBr ; CHo, is a very unstable substance, 
of no value in perfumery. The commercial article, co-bromo- 
styrolene, CgHg.CH : CHBr, can, theoretically, exist in two 
stereoisomeric forms. 

Dufraisse {Comptes Bendus, 1920, 171, 960) has prepared the 
second isomer by the action of caustic soda on bromobenzal- 
acetophenone. According to Dufraisse the two stereoisomers have 
tile following characters : — 



Specific gravity at 20° . 1-4220 

Refractive index . ' . 1-6094 

Boihng point at 22 mm. •. 107° 

Boihng point at 760 mm. 220° 
Melting point . . -f 7° 





71° (at 6 mm.) 
- 8 ° 

A. G. 

BROOM. — ^The flowers of Sarofliamnm scoparius, and pos- 
sibly allied plants, are cultivated in Provence, and the perfume 
extracted, in the form of concrete or absolute, by means of volatile 
solvents. The perfume, known as “ genet,” is also known as an 
artiflcial preparation, which usually contains some natural 
-perfume and various synthetics, including para-cresol methyl 

BRUYERB D’ANNAM. — Baechea frutescens is a plant 
formd in southern China and in Cochin China, where it is known 
as Bruyere d’Annam. It yields an essential oil having a specific 
gravity 0-890 ; optical rotation, — 4° 34' ; refractive index, 
1-4754 ; acid value, 1-9 ; ester value, 3-7 ; and ester value after 
acetylation, 44-8. It probably contains Hnalol and cymene. 
Eucalyptol is also present. This oil has also been described as 
“ essence de Bruyere de Tonkin.” The plant is in full flower in 
August. .Distillafion commences in January, and the oil varies 
to a slight extent with the locality in which it is distilled. It is 
used in France for the perfuming of 5oap. 



There appear to be two oils distilled from the plant under 
different conditions, one oil being j^ellow and the other green in 
colour. They have both been examined by Gattefosse, and also 
by Roure-Beiirand Fils {La Parfimcrie MocUrnc, 1923, 108, and 
Bulletin, Rourc-Beriraiul Fils, April, 1914, 6). The oils had the 
following characters : — 

Yelloii) Oil 

Specific gravit}^ at 15° 
Optical rotafiori . 
Refractive index . 

Free alcohols 
Aldehydes . 

Specific gravity at 15 
Optical rotation . 
Refractive index . 

Free alcohols 



. 0-8885 


. - 6° 5' . . 

— 1° 22' 

, 1-4790 


2-lG per cent. 

3-5 per cent. 

. 12-97 „ 


. 5-2 „ 

3-5 „ 

Green Oil 

° . 0-8895 


. - 0° G' 

— 4° 40' 

. 1-4772 


3-G per cent. 

1-2 per cent. 

. 11-3 


Up to 1923 tliis oil was regarded as the product of Cailicius 
fasciculata, which is now known to be erroneous. 

BUCHU OIL. — ^This oil is not used to any extent in perfumery, 
but in the preparation of flavours having a black currant odour 
or taste a small amount of it is sometimes emi)lo 3 ^ed. There are 
several species of buchu used for the distillation of the oil, of 
which the principal are Barosma scrratifolio, B. heiulina and 
B. crenulata. The leaves ^neld from 1 to 2 per cent, of oil. It 
contains limonenc, dipentene, a ketone which is probably Imvo- 
raenthono, and a crystalline body known as diosphenol, CioHjcOa, 
melting at 83°. This body occurs principally in the oil from 
B. heiulina. There is a species of barosma, B. j^Mcliella, wliich 
jnelds an oil having the odour of citronella. The four oils referred 
to have the following characters : — 

Specific gravity. 


Eofraotivo index. 

B. heiulina 

0-935 — 0-970 








1-4740— 1-4865 

B. crenulata 


— 15° 


B. serratifolia . 

0-918 — 0-960 

— 12° to — 3G° 


B. ptilchella 


+ 8° 30' 




BULNESIA SARMIENTI.— This tree yields the wood 
known as Palo santo (holy wood) or Palo hahama to the inhabitants 
of Argentina and Paraguay. The tree grows very freely along 
the course of the Rio Bermejo, a tributary of the Bio Paraguay. 
The wood yields from 4 to 8 per cent, of a semi-solid essential oil, 
w'hich is known as guaiao wnod oil or guaiacum wood oil, as it 
was at one time ei*roneously believed to be derived from Guaiacum 
officinale. It has also been knovn in commerce as champaca 
wood oil. It has a very fine and delicate odom’, and is weU adapted 
for blending vdth more powerful perfumes. Apart from its 
legitimate use, it is sometimes used as an adulterant of otto of 
roses. It melts at from 42° to 50°, and has a specific gravity 
0-9G5 to 0'975 at 30° ; optical rotation, — 3° to — 8° ; and 
refractive index, 1*5030 to 1*5050 at melting point. The only 
well-ascertained constituent present is' the alcohol guaiol, CigHooO. 

BUPLEUROL. — ^This body is an alcohol of the formula 
C 10 H 20 O* ^ found in the essential oil of Btipleurum Jrulicosu,m. 

It has a faint rose odour) and has a specific gravity 0*849 ; optical 
rotation, 0° ; refractive index, 1*4508 ; and boiling point, 209° to 
210 °. 

BUPLEURUM FRUITICOSUM.— This umbelliferous plant 
grows wild in Sardinia. The flowers and leaves contain an essential 
oil of specific gravity 0*830 to 0-8G9 ; optical rotation -f- 19° to 

47° ; and refractive index, 1*4783 to 1*48G2. It contains an 
alcohol, winch has been named bupleurol (g.v.), which has a slight 
but distinct odour of roses. (See^«. R.Accad. Lined, -1913, 22, 34.) 

BURSERA OILS.— See “Linaloe Oil.” 

twigs of this plant, also known as CalycaniJms Occidentalis, yield 
a small quantity of a fragrant essential oil of specific gravity 
0*930 ; optical rotation, + 7° ; and refractive index, 1*4710. It 
contains eucalyptol, pinene, borneol, linaljd acetate, camphor, 
methyl salicylate, and a sesquiterpene alcohol. 

BUTYL ESTERS. (See also “Butyl Phenyl Acetate.”) — 
The esters of butyl alcohol are of a fruity or floral odour, the 
principal of them having the characters shown in the table on p. 
114, as met with in commerce (Durrans, P. ds E. 0. B., 1924, 226). 

BUTYL PHENYL ACETATE.— This ester, of the formula 
C 4 HgC 02 .CH 2 .CeIl 6 , is a colourless oil having an odour recalling 
that of carnation. It is only used in small quantities, and gives 
s* 113 



Specific gravity. 

Eefractivo index:. 

Boiling point. 

Butjd acetate . 

0 - 880 - 0-882 


i 23 °- 127 ° 

,, benzoate 

1 - 0085 - 1-0090 

1 - 4975 - 1-4980 

247 ° 

„ bul3U’ate 



160 °- 165 ° 

„ formate . 



106 °- 107 ° 

,, phenjd acetate . 



260 ° 

„ propionate 



145 °- 146 ° 

„ salicylate 



266 °- 207 ° 

„ valerianate 



170 °- 175 ° 

character to the various types of carnation bouquets. Its isomer, 
isobutyl phenyl acetate, is of a much finer odour, and is known 
as “ eglantine ” or “ ideal base.” It is used as the basis of most 
perfumes offered under the name “ eglantine,” and is also useful 
in carnation and rose odours. It has a specific gravity 1-104, and 
refractive index 1-5570. 

BUTYRIC ALDEHYDE, — ^Butyric aldehj^de, C 3 H;.'COH, is 
an aldehyde with a pronounced sharp odour, occurrnig in oils of ' 
eucalyptus and cajuput. It is a liquid, boiling at 75°. 

BUTYRIC ETHER. — See “ Ethjd Butju'ate.” 

CABRIUVA WOOD OIL. — Myrocarims fasiigiatus is a 
member of the natural order Leguminosce, a native of Brazil. 

It is know'n locally as cahriuva. The flowers are yellowish-white 
and of great fragrance. Their odour resembles that of a mixture 
of vaniUa and frankincense or tolu balsam. The wood is highly 
valued in Brazil. 

Schimmel c& Go. {Report, April, 1896, 64) examined the oil, 
and found it to have a specific gravity 0-9283, and optical rotation 
— 8° 29'. 

CABUREIBA BALSAM OIL. — Myrocarpiis frojidosus and 
M. fastigiaius (see also “ Cabriuva Wood Oil ”), both natives of 
Brazil, and belonging to the natural order Leguminosce, yield a 
balsam from natural as weU as from artificially produced woimds. 
The balsam is reddish-brovoi, and greatly resembles Peru and 
tolu balsams, both in appearance, consistency and odour. It 
contains benzoic acid, both free and combined in the form of 
esters. Vanillin is also present in traces. 

CADE, OIL OF. — See ” Cadinene.” 


CADINENE. — ^This sesquiterpene is found principally in oil of 
cade, the product of the destructive distillation of the wood of 
Jiniipcnis oxiiccdrus. From the tar so produced, a refined oil can 
be obtained by steam distillation. Tliis is a dark yellow viscid 
liquid of specific gra%dt\'' O-Olo to 0'930, and optical rotation 
about — 30®. It contains much cadinenc, CigHoj, a liquid of 
specific gravity 0'921 ; optical rotation, — 105° ; refractive 
index, 1-5065 : and boiling point, 273° to 275°. Cadinene yields 
a fine blue colour when a few drops are dissolved in chloroform 
and the liquid shaken vith a few drops of concentrated sulphuric 
acid. It is present in numerous essential oils, including patchouli, 
cedar wood. West Indian sandalwood, and others. It is used in 
small amount in perfumery, and has been recommended as a 
constituent of artificial ylang-ylang oUs. 

CALAMINE. — Calamine is essentially zme carbonate, and is 
used in the preparation of dusting powders and face lotions. 
Originally the term calamine indicated the natural mineral very 
finely powdered. It is a hemy powder of a brownish to pinlc 
colour, consisting of zinc carbonate, uith varying quantities of 
zinc silicate and traces of iron oxide as impurities. To-day the 
calamine of commerce is usually artificially precipitated zinc 
carbonate, with varying proportions of zinc oxide and traces of 
ferric oxide to colotu it. The only important feature for the 
perfumer is that it should be finely powdered, free from gritty 
particles, and should consist almost entirely of zinc carbonate, 
ZnCOs, and be soluble in hydrocliloric acid with the exception of 
a small amount — ^not more than 3 to 5 per cent, in the best 

CALAMINTHA OILS . — Galamintlia nepela {Sakireja Cala- 
mintha) is a plant flourishing in Calabria and Sieily, and from 
which the essential oil has been distilled. The plant is known as 
“ false mint,” or “ nepitella.” Sicihan plants examined by Roiire- 
Berlrand Fils {Bulletin, October, 1912, 68) yielded 0-14 per cent, 
of essential oil. Umney and Bennett also examined a Sicilian 
oil {Chemist and Druggist, 67, 970). The figures obtained for these 
two samples were as follows : — 


Specific gravity . 0-925 

Optical rotation . -{- 17° 48' 

Esters . . . 4-4 per cent 

Alcohols (as menthol) 14 „ 

Ketones . . .20 „ 


-t- 14® 

4-2 per cent. 




8 — 2 


La Face has recentlj’’ examined authentic samples of this oil, 
and found quite similar figures, although a sample of French grown 
oil is reported as having a specific gravity 0*982 ; optical rotation, 
+ 3° 6' ; and refractive index, 1*5115 {La Parfumerie Moderne, 
1923, 162). 

Galamintha wnhrosa grows wild in certain localities in Travan- 
core, and is known locally as JcarimiJmmha. K. L. Moudgill 
{Jour. Soc. Ghem. hid.. May 23rd, 1924) distilled a quantity of 
fresh leaves with steam, when a 0*35 per cent, yield, calculated 
on the dry leaves, of a light j^'cllow oil possessing a strong rather 
complex, but not unpleasant odour, was obtained. The oil had 
the follovdng characters : d^, 0*8854 ; — 1-4760 ; = 

— 45*2° ; acid value, 0*5 ; ester value, 15*9 ; ester value after 
acetylation, 40*7 ; aldeh3’-des by the neutral sulphite method, 
6*5 per cent. The oil was insoluble in 80 per cent, alcohol, sparingly 
soluble in 85 per cent, alcohol, soluble in 90 per cent, alcohol. 
In view of the low density and refractive index of the oil, the 
difficulty with which it dissolves, even in 85 per cent, alcohol,- 
and the ester values, it would apjoear to consist mainly of hj^dro-. 
carbons. The oil dried over anhj^drous sodium suljDliate was 
distilled under reduced pressure, first over a boiling-water bath 
(fractions 1 to 3), and then rapidly over a free flame, and the 
following fractions Avere obtained : — 


Boiling point. 



per cent. 


To 80° 




- 62*5° 






- 68*3° 


Above 85° 




— 53-8° 


105°-110° . 




— 5*2° 


Residue and loss 


(by diff.) . ■ . 




Fractions 1, 2 and 3 would appear to contain the same com- 
pound. Fractions 1 and 2 were mixed and distilled repeatedly 
over sodium under atmospheric pressure, and finally 12 c.c. of 
a colourless oil were obtained, of boiling point 176° to 177° ; 
d~s; 0*8565 ; = 1*4700 ; = —73*35°. Z-Limonene has 

boiling point 175° to 176° ; d, 0*8472 ; — 1*4746 ; =■ 

— 105°. Bromination of the oil yielded a halogen derivative 
which proved to be Z-limonene tetrabromide. In spite of repeated 



fractionation and distillation orer sodium, the /-limonene separated 
from this oil \^’as heavier, but had a higher refractive index 
than pure Z-limonene, probably due to the presence of small 
ouautities of another hydrocarbon, which, however, could not be 

Fra^'iion 4. — ^The aldehyde content of this fraction was found 
bj' the sodium bisulphite method to be 10 per cent. The residual 
oil had == 1.4930 ; = -}- 5-4° ; d%, 0-9293. It was 

soluble in 3-4 volumes of 75 per cent, alcohol. 

CALYCANTHUS OIL. — ^Thc air-dried stems of Cahjeanthus 
floridus 3 'ield a small quantity of an odorous essential oil, which 
has been examined b}* Miller, Taylor and Eskew {Jour. Amer. 
Chem. Soc., 36, 2182). Pinenc, cineol, bornyl acetate and other 
esters are present in the oil, and probablj’- linalol and sesqui- 
terpenes. Tlrrce samples had the following characters : — 






Yield .... 

0'63 per cent. 

0-25 per cent. 

0‘39 per cent. 

Specific gravity at 25° . 




Optical rotation . 

-f 2-85° 



Eefractive index at 26° . 




Saponification value 



; 16-6 

Saponification value after 



Total alcohols, as borneol 

18-41 per cent. 


' 14-46 per rent. 

Enters, as bornyl acetate 

4-37 ., 

5*04 per cent. 

5-81 „ 

Cineol .... 




CAMPHOR AND CAMPHOR OIL. — Camphor is a con- 
stituent of numerous essential oils used in perfumery, but, as such, 
is only used in the industry for the preijaration of such substances 
as camphor ice, etc. Camphor oil, however is of great importance 
as the source of supply of a very i.npori;ant raw -uaterial of the 
perfume industry, namelj’’, safrol (g'.r’.). The tree yi.elding camphor 
oil is Ginnamomum campliora. It is widely distributed throughout 
the eastern provinces of central China, on the island of Hainan, 
and very extensively in Formosa. It also occurs as a forest tree 
on the islands of Kliusliiu and Shikoku. The greater part of the 
camphor produced comes from Formosa, and the industry is 
practically a Government monopoly. The tree is felled and the 
young branches and twigs are chopped up and placed in perforated 



jars and heated over steam. The steam satiirates the fragments, 
and the crude camphor sublimes into earthenware pots placed 
over the jars. The crude material is pressed and separated into 
a slightly more refined camphor, and a certain amount of camphor 
oil. The greater part of the camphor oil of commerce is, however, 
obtained by direct distillation of the chips in crude stills. The 
oil is drained from the separated camphor, but still retains 
a considerable amount in solution. Kedistillation is resorted 
to until it does not pay to separate the camphor any further. 
So that, in fact, solid camphor is really o:^y a fraction of 
the entire camphor oil,” and the camphor oil of commerce 
is really only the residual fractions after the extraction of most 
of the camphor. 

Camphor, HjgO, is the ketone of the alcohol borneol (g'.u.), 
and occurs in the essential oil as fZc.rb-o-camphor, the rare Icevo- 
camphor being found in the oil of Matricaria 'parllicnixim. It forms 
a translucent mass, obtainable in coarse powder by subhmation, 
of specific gravity 0-985 ; melting point, 176° to 179° ; boiling 
point, 205° to 207°; and specific rotation, 44°. It is freely 
soluble in organic solvents (alcohol, 1 in 1 ; chloroform, 4 in 1 ; 
ether, 2 in 1). It occm's in commerce in coarse powder (fiowers 
of camphor), in bell-shaped masses (beU camphor), or in small 
tablets of varying sizes. In the semi-refined condition it is also 
imported in the form of large slabs. ■ 

The crude camphor oils of commerce exist in, roughly, four 
different varieties. These are as follows : — 

(1) The crude oil as it leaves the distillery, -with as much 
camphor separated as possible. This has a specific gravitv 0-950 
to 0-998. 

(2) Heavy camphor oil, or brovm camphor oil, which is the crude 
oil from which the low-boiling terpene fractions have been as 
completely removed as possible. This oil is rich in safrol. Specific 
gravity, 1-000 to 1-040. 

(3) The light oil, consisting of the terpene fraction mentioned 
under (2). Specific gravity, 0-870 to 0-890. 

(4) The very high-boiling fractions, extremely rich in safrol, 
of specific gravity 1-060 to 1-075, and which is sold as/‘ artificial 
sassafras oil.” 

Safrol, obtained from camphor oil, is the raw material from 
which heliotropin is manufactured. 

A very large number of patents have been granted for the 
manufacture of camphor artificially. A clear . distinction must 



be made between tlie true artificial camphor, the so-called 
“ p\-nthetic camphor,” and pinene hydrochloride. Cm HmHCl,a 
crj'stalline compound of pinene which was knowm as artificial 
camphor, on account of its physical resemblance to true camphor, 
before the artificial production of camphor had been achieved. 
This so-called artificial camphor is prepared b}’- passing a current 
of dry hvdrochloric acid gas thi’ough well-coolcd pinene. The 
resulting crystals melt at 127°, and have a camphoraceous odour, 
and may be used as a substit/utc for camphor to a certain extent. 
A complete sj-nthesis of camphor has been achieved by Komppa 
{BcricMc, 36,' 1332), but has no commercial application. Jlany 
processes jdeld camphor on a reasonably paj'able scale, but, 
owing to tlie fact that the Japanese monopoly is able to control 
prices, artificial camphor is rarely able to compete with the 
natural substance. In general, such processes for the production 
of artificial camphor depend on the conversion of pinene, obtained 
from turpentine oil, into pinene hj'drochloride, which, bj’’ abstrac- 
tion of hydrochloric acid, jdelds camphene. This is converted 
into isobornjd acetate bj' treatment with acetic and sulphuric 
acids, and is saponified by treatment with allcali, and the resulting 
isoborneol is oxidised to camphor. 

(See also “ Sho-Gjm and Yu-Ju Oils ” ; refer B. J. Eaton, 
Dejyt. of Agricvllwc, Federated Malay Stales, Bull. 15, February, 
1912, for attempts at cultivation of camphor trees in Malay 
States ; and see photographs of stills by Monopoly Bureau of 
Formosa, reproduced in Parry, “The Chemistry of Essential 
Oils,” 4th ed., vol. ii., pp. 158, 159. For the liigh-boiling sesqui- 
terpene compounds of camphor oil, see Ruzicka and Stoll, Helv. 
GMm. Act., 1924, 7, 260.) 

CANANGA OIL.— Oil of cananga and oil of ylang-ylang are 
obtained from the same botanical source, the superiorit}’’ of the 
ylang-ylang oil being due to the different conditions under wliich 
the trees grow, and to the methods of distillation. The tree from 
wliich the flowers are distilled is Cananga, odorala, one of the 
Anonaeeoi, of which a native name is Alan-guilan, or Ililang- 
Ihlang, meaning the “ flower of flowers.” 

The tree is a native of Ava and Tenasserim, and is generally 
distributed and cultivated throughout southern Asia. It attains 
a height of about 60 feet. The flowers are very handsome and 
conspicuous, bell shaped, of a pale yellow or greenish colour, with 
a beautiful perfume, often compared with a mixture of hyacinth, 
na»’cissus, clove, jasmin and lilac. 

- 119 


The following account of the plant is from the Perfumery and 

Essential Oil Eecord, 1910, 223 ; , , r; 4 . 

“ The plant from which it is derived, Cananga odorata, was farst 

described by Enmph in 1750 under its Malayan designation of 
Bonga cananga. It is called Isjampa by the Javanese. It is 
stated to have been first introduced into India from Sumatra m 
1797 a description of it in the Botanical Gardens of Calcutta 
being by Boxbm’gh (‘ Flora Indica,’ 1832). It is described by 
Hooker and Thompson (‘ Flora Hidica,’ 1855). It is lUustrated in 
the ‘ Flora Java ’ by Blume (1829). We arc courteously informed 
by IMr. Prain, the director of the Hoyal Botanical Gardens at 
Kew, that no flowering plants are avafiable for photography at 
the present time. Fluckiger (Pharm. Jour., May 14th, 1881) 
stated that the incorrect name Unona odoraiissima so ^dnscribed 
from its overpowering odom’ — originated vdth Blanco ( Flora de 
Filipinas,’ Manila, 1845), and for years the oil was described in 

price lists as oleum unoiiffi. ^ ■ .or a 

'' The oil appears to have been sent to Europe first m 1864:, 
when it was offered in Paris. The first shipments were not made 
from klanila, but the recognition of its beautiful odour resulted 
m its distillation in Manila, at first by German pharmacists. 

“ Cananga odorata attains a height of 60 feet, has few, but much 
ramified, branches, and handsome tea-shaped flowers, which droop 
elegantly. The blossoms grow in every month of the year, but 
contam most oil in the months of June to December. The tree is 
common to many localities, but is found principally in weU- 
populated districts, where it appears to thiive best. The reason 
for this has not been definitely ascertained, but it appears to be 
accurate and constant. It is propagated by planting seedlings 
or cuttings about 20 feet apart, which grow very rapidly, fiowermg 

in the tliird year. ■ . . t ^ 

“ In Manila the petals are subjected to the simplest form 

of distillation, the oil being divided into two or more portions, 
the first clear and delightfully fragrant, the later distillate 
yellowish and frequently empyreumatic. It is stated that, 
to obtain a prime quality of essence, 300_to 350 1b. of flowers 
would be needed as to season and maturity of flowers to yield 

1 lb. of the oil. i t 1 ;+ 

“ The Java oil distillation has been described by De Jong after 

an official visit of mspection to Serang. The petals are stated 
to have been pounded before distiUation, the resulting oil contain- 
ing more sesquiterpenes, and being less fragrant than the Manila 



oil. The methods of distillation have been much improved, vith 
a corresponding improvement in the oil. 

“ In the distillation in Keunion no separation of the oil was 
made until recently, the idea being to obtain a high percentage 
3 'ield rather than delicacy of odour, and, according to figures 
communicated to us, the yield is freq^uently as high as 2 per cent. 

“ The distinction between cananga oil and 3 dang- 3 dang oil is 
not sharply defined. The former usually consists of the higher 
fractions containing a greater proportion of sesquiterpene, but in 
some districts the entire oil is sold as cananga oil. 

“Ylang-jdang oil is the finest grade, consisting of the first 
fractions of the oil, and containing a greater proportion of 
ox 3 ’'genated constituents.” 

The cultivation of the tree reaches its maximum degree of 
perfection in the Plulippine Islands, the finest oil being distilled 
in Manila. A considerable amount is also distilled in the island 
of Reunion, and a good deal of oil of less fine quality comes from 
Java and the neighbourhood. Commercially, the oil distilled in 
the Philippines is ylang-jdang oil par excellence. The oil from 
Reunion is usually termed ylang-ylang, but is not of such fine 
odour as the Manila oil ; whilst the Java oil is known as 
cananga oil. 

As there has been much confusion over this oil, the following 
account of it, due to R. P. Bacon {PMlipp. Jour. Sc., 3, 108, 65), 
vdU be of interest : — 

In Manila, where the conveniences for careful distillation are 
greater than in outlying districts, fine oils as well as second-class 
oils — ^v'hich are frequently known even there as cananga oil — 
are produced, but in the provinces the distillers, who are com- 
pelled to work with less scientific apparatus, generally produce 
only a second-class oil. Quite three-fourths of the blossoms 
delivered at Manila are green and unripe, although it is of the 
highest importance to use the ripe yellow blossoms for the best 
quantity and yield of oil. There has been much mystery made 
over alleged trade secrets connected with the distillation of this 
oil, but Bacon does not consider any such secrets exist. The 
great mistake distillers make in the provmces is burnhrg the 
'flowers in the still and wrongly selecting the fractions of the oil 
distilled. They attempt to get 1 kg. of oil from 150 to 200 kg. 
of flowers m one bulking, whereas they should only obtain 1 kg. 
of the finest oil from 400 kg. of flowers, and then about the same 
quality of second grade oil. The industry is also an important 



one in BeTinion, and here again it has been shown that by a 
short-time distillation the smaller amount of oil is compensated 
by the fine quality. 

Small quantities of the oil are produced in Madagascar and in 
the Seychelles Islands. 

The climatic and soil conditions, coupled with the considerations 
above noted, account for the difference in the quality of the various 
oils. Bacon has examined a number of' Pliilippine oils, and gives 
the following figures : — 

Second quality. 

First qualit3L 

Specific gravit 3 ’' at 30° /4° . 



Refractive index at 30° 



Optical rotation 

- 27° to - 49*7° 

- 27*4° to - 87° 

Ester number . 


(in one case 169) 


Bacon classifies the oils as follows. First-class oils usually have 
an ester number over 100, a refractive index not above 1*4900, 
and optical rotation rarely over — 45°. Low values for optical 
rotation and ester number usually indicate low-grade oils. 

The usual analytical values for Reunion and Java oils are as 
follows : — 



Specific gravity at 15° 



Optical rotation 

- 34° to - 65° 

— 15° to — 52° 

Ester number 

96 to 160 

10 to 60 

Refractive index at 20° 

1*5000 to 1*5100 

1*4900 to 1*5050 

Artificial 3 dang- 3 dang oil is a commercial product. The principal 
bodies used in its preparation are ^jara-cresol meth 3 d ether, linalol, 
geraniol, isoeugenol, benzyl acetate, benz 3 d benzoate, isoeugenol 
meth 3 d ether, methyl benzoate, benzyl alcohol, and methyl 

Adulteration of 3 dang- 3 dang or cananga oils vdth benz 3 d 
benzoate is a question of considerable difficulty to the analyst, 
as benz 3 d benzoate is, in certain proportions, a natural constituent 
of the oil. J. C. Umney (P. cC? E. 0. R:, 1914, 37-86) gives the 



folloT\’iiig figures for a number of samples of various origins wliicli 
he examined : — 


1 Bourbon, 


Specific gravity , . 1 



Optical rotation 

— 38° to — 51° 

— 39° to — 41° 

Refractive index . . : 



Ester number 



Non-volatile residue (on 
water bath, in 2 hours) . 

4-3-1 6-4 jier cent. 

25-1-40-3 per cent. 




Specific gravity 



Optical rotation 

- 30° to - 42° 

— 48° 

Refractive index 



Ester number 



Non-volatile residue (on 
water bath, in 2 hours) . 

16-9-29-3 percent. 

14-19 per cenl . 

If, however, the oil is heated on a water bath until no further 
loss in weight is noted, any non-volatile residue over 7 per cent, 
should be regarded with suspicion. Further, the non-volatile 
residue should be saponified, and if the saponification value varies 
outside the limits 65 to 100, the oil is probably adulterated. If 
fatty oils have been used as adulterants, the saponification value 
will be much higher, and the residue must be examined for fatty 
acids, which can be separated and their molecular weight deter- 
mined, which win indicate the origin of the adulterant. 

Umney found that in the case of the finest Manila oils the 
residue does not usually exceed 6 per cent., although inferior oils 
contain more than this. The evaporation on the water bath should 
be continued for at least eighteen hours, as benzyl benzoate is 
very slowly volatilised at water-bath temperature. 

Roure-Berlrand Fils {BvMetin, April, 1910, 61) give the table 
on p. 124 as typical figures for various ylang-ylang oils. 

The foUoAving references are to important papers on the oil, 
where further details may be found : — 

(1) ” East African lhang-Ylang Oil ” {SchimmeVs Report, 
October, 1911, 102). 





— 42° 12' 

1 voL, then 


per cent. 



per cent, 


per cent. 


per cent. 

(2) “ Reunion, Nossi-Be, Mayotte, and Manila Oils ” {Roure- 
Berirand Fils, Bulletin, April, 1910, Gl, and October, 1911, 40). 

(3) “ Sej^clielles Ylang-Ylang Oil ” {Bulletin of the Imperial 
Institute, per “ The Clieinistry of Essential Oils ” (E. J. Parry), 
4tli ed., vol. i., p. 520), 

CANARIUM RESINS. — ^Tlierc are a number of resins or 
oleoresins known under the name elemi. hlost of these are the 
product of Canarmm species, but the resinous matter most 
commonly known as elemi is the substance collected in the 
Phihppine Islands, principally from Ganarivm luzonicuni, and 
possibly from G. commune. TJiis is kno^vn in commerce as Manila 
elemi. It contains from 15 to 30 per cent, of essential oil of 
some perfume value. The oleoresin is used as a fixative, but should 
be used in the form of an alcoholic tinctm’e from which the 
insoluble matter has been rejected by filtration. When fresh, 
Manila elemi is pale yeUow in colour, soft and granular, somewhat 
resembling crystallised honey in appearance. The general 
characters of the oleoresin vary 'svith the district m which it has 
been produced, the soft and hard varieties having the foUovdng 
characters : — 

Soft. Hard. 

Volatile oil . 15-30 j)er cent. ., 8-9 per cent. 

Ash . . 0-02-0-2 „ . 0-2-1 

Acid value . 17-25 . . 15-28 

Ester value . 7—25 . . 25-28 


Specific gravity at 15° 0. 0-9492 

Rotatory power . — 38° 8' 

Solubility in 90 per/ 4 vol., then 
cent, alcohol . \ cloudy. 

Acid value . . — 

Saponification value . 96-03 

Esters, as linalyl J 33-6 

acetate . . ( per cent. 

Saponification value \ jsg.H 

of the acetylated oil J 

Total alcohols (as ( 40-3 

linalol) . . I percent. 

Combined alcohols { 

( per cent. 

fill ( 13*9 

Free alcohols . - cent. 




/0-911 to 

\ 0'958 

— 47° 40' 

1 vol., then 

1—27° to 
( — 49-7° 


/ “ 




90 to 138 


per cent. 

} - 




per cent. 




24-7 to 38 

per cent. 

per cent. 



per cent. 

/ “ 



Tlie essential oil is a fragrant liquid recalling the odour of mace, 
and having the folldudng characters : specific gravit3^ 0-870 to 
0-915 ; optical rotation, + 30° to + 55°, but rarelj^ + 4° to 
134° ; refractive index, 1-4775 to 1-4900 ; acid value, 0 to 2 ; 
and ester value, 4 to 10. The oil is very variable in composition. 
The foUoving constituents have been detected in twenty-one 
.samples examined by Clover (Amer. Ghem. Jour., 1908, 39, 613) : 
limonene, phellandrene, pinene, terpinene, and terpinolene. A 
sesquiterpene alcohol, elemol {q-v.), is also present, and a small 
amount of a phenol ether which has been named elemicin. 

CARAWAY OIL. — This oil is obtained by the distfilation of 
caraway fruits, the product of Cariim carui, a plant found in 
northern and central Europe. It is erdtivated in various countries, 
especially in Holland. The name caraway and the Spanish name 
alcaraliueya. are derived from the Arab Icarawya. The fruits 
yield from 3 to 7 per cent, of essential oil having the following 
characters : specific gravity, 0-907 to 0-918 ; optical rotation, 
70° to -f 83° ; refractive index, 1-4840 to 1-4890 ; and contain- 
ing 60 to 60 per cent, of carvone. 

Caraway oil consists almost entirely of carvone (carvol), 
Cio H14O, and the terpene limonene. Its value depends on the 
carvone, so that it may be approximately valued by its specific 
gravity, that of carvone being 0-964, and that of hmonene 0-848. 

The best method for the determination of carvone is the neutral 
sulphite method {vide “ Aldehydes, Determination of ”). If the 
oil be fractionally distilled, not more than about 25 per cent, 
should distil below 180°, and from 55 to 65 per cent, should distil 
above 200°. 

On the Continent pure carvone is largely employed in place of 
caraway oil. Hence there is a considerable amount of caraway 
oil available from which much of the carvone has been abstracted. 
Some of these oils are standardised to the lowest limits that the 
various pharmacopoeias give for the oil ; others have so much 
carvone abstracted that they can only be sold as “ light ” caraway 
oil or, in common with the oil distilled from the chaff and dust 
left after tlireshing the seed, as “ caraway chaff ” oil. These 
light oils are employed in cheap soap perfumery. A stfil lower 
grade o'il is sometimes sold under the name “ carvene.” This is 
merely impure limonene with a slight caraway odour, and consists 
substantially of the terpenes of caraway oil. 

CARDAMOM OIL. — ^Traces of cardamom oil are sometimes 
used in eau de Cologne and in artificial lily perfumes. The 



ordinaiy cardamom is the fruit of Eleitaria cardamonium, one of 
the Zingiheracem, Although the plant grows wild in the forests 
of southern India, where it is commonly known as hachi, the bulk 
of the fruits of commerce are provided by cultivated plants, and 
Ceylon supj)lies the greater part of the cardamoms used. Some 
of the cardamoms met with are the product of one or more 
varieties of the plant, and yield essential oils which differ between 
themselves. The writer (E. J. P.) has distilled the oil from the 
so-called Ceylon-Malabar and the Ceylon-Mysore seeds. The 
former jdelded 1'3 jDer cent., and the latter 2*6 per cent., of essential 
oil. The odours of the two oils were practicaUj’’ indistinguishable. 
The folloAving figures cover those of most pure samples : specific 
gravity, 0-923 to 0-945 ; optical rotation, -f 24° to -}- 48° ; 
refractive index, 1-4620 to 1-4675 ; and ester value, 90 to 150. 

The oil contains terphtyl acetate, terpmeol, and limonene. 

(See also E. J. Parry, “ The Chemistry of Essential Oils,” 4th ed., 

vol. i., J)- 101 ; Sawer's “ Odorographia,” 2nd series, jd. Ill ; 

and Eidle}’-, “ Spices,” p. 324.) 


CARNATION. — Tlie carnation is merely a varietj’ of the 

clove pink Dianihvs cargogjliyllvs, the species including carnations, 
pinks and picotees. The rich odour of the less highty cultivated 
varieties of the clove and carnation has alwa 3 ’’s been exceedingl}’" 
popular. In the more higlily cultivated flowers perfume has given 
wa}'^ to form and colour, as in the case of the rose. A certain 
amount of the natural perfume is extracted in the south of France, 
principally in the form of a pomade, although a little concrete or 
absolute reaches the market. The buUc of the carnation perfume, 
however, is based on synthetics, rounded off with natural flower 
perfumes and fixatives. According to a writer (anonymous) in 
the Perfumery ami Essential Oil Record, 1917, 18, nearly all the 
species of Dianilms are natives of Em’ope, tropical Asia, and 
northern Africa. In France, where it is knovm as (Eillet, it is 
largely cultivated for decorative purposes. It is a beautiful plant, 
remarkable not onl}^ for its perfume, but for the colour and 
elegance of its flowers. Some 2,000 varieties have been produced 
by cultivation, of which the following may be mentioned ; 
Alegatiere (vivid red flowers), Antoine Devert (cerise coloured), 
Commandant Riviere, Comtesse de Paris (yellow’^), Fran 5 ois 
Buchner (bright red). General Boulanger (vivid red), Hugues 
(abundant red flowers), Jean Sisley (red and yellow). La Fontaine 
(yellow, striated), L^on Aurange (bright cerise), Madeleine Solignac 
(lilac rose), Mahonais (flesh coloured, flourishing in winter and 



earij spring, cultivated round Toulon), Enfant de Mce (red or 
vliite flowers), Pauline Borriglione (rose or salmon pink). President 
Carnot (purple flowers). Rose Bivoire (rose coloured). Souvenir de 
Pifine Llari (wdiito flowers), and Souvenir de Madame Gobet 
(yellowisli copper coloured). 

Other varieties which flomish in winter are Auguste Vernier, 
Capitame Berner, Laverriere, hladame de Presle, Oriflamme, 
Raphael, and Roi des Rouges. 

C^dlivatwn . — Carnations flourish best in a w’ell-di-ained soil 
vith free access of air and sheltered from the sun. Thej’' are 
reared from seed, and from layers or suckers. Seeds are sown in 
autumn or spring in earthenware pans or pots. AVlien sovti from 
March to May, the young plants may be planted out about 
fourteen months afterwards, when they possess five or sis: leaves, 
care being taken to protect them from the sun’s raj^s and from 
cold and damp. To obtain autumn or winter flowers, the seeds 
are sown in autumn. Slips should be planted in a light sandy 
soil in pots, leafy branches being preferable for this operation. 
The slips will root in thirty to forty days. Layering is effected 
by embedding the branches near a node, after making a sma.I] 
longitudinal incision before burjdng them. This favours the 
development of roots. The branches are kept in place by means 
of small pieces of wood. Durmg the summer the extremities of 
branches which tend to lengthen are pinched, in order to render 
the plant more vigorous and retard flowering. Erom time to 
time lic[uid .manure should be applied to obtain a greater 
abrmdance of flowers. 

A clove-scented perfume is also developed in the flowers of a 
convolvulus found in the forests of Mednapore, in Bengal, which 
is botanically knovu as Letlsonia hona-nox (Roxburgh). The 
flowers are large and white, expanding at sunset and withering 
at sunrise ; they are produced during the rainy season. 

Another clove-scented convolvulus is the Iponicea grandiflora 
(Roxbm-gh), knovm in Bengal as Doodiya-Kulmi. This plant 
twines. to a height of 20 feet, and bears white flowers 4 to 6 inches 
in diameter. It is common in hedges in Samulcota and on the 
banks of watercom’ses. It is closely allied to the Lettsonia hona-nox. 

A clove odour is strongly developed in the bark of Laurus 
culilawan {Laurus Carophyllata), and in Cinnamomum sinfox. The 
bark of Cimiamomum culilawan, a native of Amboyna, is called 
“ clove bark ” oh account of its strong odour of cloves. “ Clove 
cassia ” is the name applied to the bark of Dicypcllium Garyophyl- 



latum, wliicli is also known as Brazilian clove bark. It is found in 
Para and Bio Negro. The Madagascar clove nutmeg is the fruit 
of Agatliophyllum aromaiicum, a laurel the leaves of which are 
used the natives as a condiment. 

The actual basic material for artificial carnation is isoeugenol 
iq.v.), usually mixed vdth some eugenol. Hexyl-methyl ketone, 
isobutyl-phenyl acetate, benzyl acetate, phenyl-acetic aldehyde, 
and terpineol are also often employed in judiciously small amount, 
with a Httle benzyl isoeugenol as a useful fixative. A useful 
variation in “ shade ” of the odour is produced by the use of a 
httle methyl eugenol and methyl isoeugenol. 

The essential oil of the carnation has recently been examined 
by Ghchitch {Bull. Soc. Chim., 1924, iv., 35, 205). The yield is 
only about 0-003 per cent, calculated on the fresh flowers. The 
oil is a pale green sohd of intense odour, which, until heavily 
diluted, does not resemble the odour of the flower. It melts at 
35° to 37°, and has a specific gravity 0-869 at 40° ; optical 
rotation, — 8 ° 28' ; acid number, 4-9 ; ester number, 61-3. It 
contains 31 per cent, of a stearoptene, which is probably hepta- 
cosane, C 27 H 5 Q, melting at 53° to 54°. Traces of an aldehj^de are 
also present. 

CARROT, OIL OF.— See “ Daucus, Ofi of.” 

GARVAGROL. — ^This body is a phenol, of the formula 
C 10 HJ 4 O, isomeric with thymol. ChemicaUy it is isopropyl-ori/jo- 
cresol. It is fomid, frequently in association with thjunol, in 
various thjune and origanum oils. It also results artificially from 
the treatment of carvone by potash. It is a colourless oh of 
fragrant, refreshing odour, sohdifying at about 1°, boiling at 236°, 
of specific gravity 0-981, and refractive index T5240. 

CARVENE.— See “ Caraway Oil.” 

CARVONE. — Carvone, C 10 H 14 O, is a ketone, the characteristic 
odour bearer in oils of caraway and dill, in which it occurs as 
cZea-fro-carvone. It is found as ZcEvo-carvone in kuromoji oil. It 
is an odorous liquid of specific gravity 0-964 ; optical rotation, 
-f 59° 30' ; refractive index, 1-5020 ; and boiling point, 224°. 

GARYOPHYLLENE. — ^This body is a sesquiterj)ene, C 15 H 24 , 
occurring in oil of cloves and several other essential oils. There 
are several isomeric bodies known under this name which are 
of considerable interest to the chemist. But from the perfumer’s 
point of view the mixture of sesquiterpenes obtained from oil 

12 s 


of (Aorc^ ^vhoii ilic cugenol lias been almost complctel}^ extracted 
h' Lnov.’ii as carvopliyllcnc. This mixture has a specific gra\ity 
from 0-P05 to 0'910 ; optical rotation, — 7° to — 9"^ ; refractive 
iivlex. about l-oOlO : and boiling point, about 258° to 2G1°, With 
a little cuacnol left in the mixture, it is the light clove oil sold 
for clicap soap perfumery. 

CASCARILLA. — The ca^onrilla bar!: of commerce is tlie bark 
of C/'o!o?i Elciflcvif'ij and possibly" that of Crofoit CcisccivUlci, Tlic 
lives arc indigenous to the Rahama Islands. The bark has a 
pleasant aromatic odour and burns with an exceedingly fine 
fragrance, so that it often used in fumigating or incense compo- 
sitions. It yields from 1 to 3 per cent, of essential oil, which is 
occasionally used in jicrfuniery, and wliich has the following 
characters': specific gravit3% 0-895 to 0-92S ; optical rotation, 
+ r to d- 12°; refractive" index, 1-4910 to 1-49G0 ; and ester 
number, G5 to 75. The perfume constituents have not been 
identified, but it contains a scscjuilcrpcne alcohol, C15H0.JO, and 
an acid isomeric with undccjdcnic acid. 

CASSIA OIL.— Cassia oil is the distillate from the leaves, 
twigs, and other portions of Cimunnoimnn cassia, the so-called 
Chinese cinnamon, which is probably a native of Cochin China. 
It is chiefiy cultivated in China proper, the three principal districts 
being /laiwu in the Kwangsi province, Lupko, and Loting in 
the Kwangtung province. In a report on a journe}- to Kwangsi 
by H. Scliroelcr in 1897, the wnter staled that the shrubs destined 
for the production of the Cassia lignea, as the prepared bark is 
tenned, are partly stripped during the summer months of their 
smaller branches and their juic^^ leaves. These are then boiled 
in large vessels, and the cassia oil recovered 133" a primitive S3'’stcni 
of distillation. An interesting account of the origm of tlic oil is 
contained in a paper in the Jouvnal of the Liniican Soo'icly, 
December, 1882. The distilleries are situated in valleys where an 
abundant flow of water for condensing purposes is available. 
If leaves only are used for distillation, the oil is of the finest 
quality, so that, as a rule, only about 30 per cent, of twigs are 
used vdth 70 per cent, of leaves. A typical oil so distilled was 
found by Niedliardt to contain 8G per cent, of cinnamic aldeh3^de, 
the principal odorous constituent of the oil. A specimen distilled 
entirely from the bud sticks was found by ScMinmcl cO Co. to 
contain 92 per cent, of cinnamic aldeb3’'de, and the following 
results “were obtained from various -parts of the plant : (1) Cassia 

r. 129 0 


bark : yield, 1-5 per cent. ; specific gravity, 1-035 ; cinnamic 
aldeli3^de in the oil, 89 per cent, (2) Cassia buds : yield, 1-55 per 
cent. ; specific gravity, 1*026 ; cimiamic aldehyde in the oil, 
80-4 per cent. (3) Cassia bud sticks : yield, 1-64 per cent. ; 
specific gravity, 1-046 ; cinnamic aldehj^de in the oil, 92 per cent. 
(4) Cassia leaves, stalks, and twigs : yield, 0-77 per cent. ; specific 
gravity, 1-055 ; cinnamic aldehyde in the ofi., 93 per cent. 

Cassia oil is imported chiefly from Hong Kong in “ leads ” — 
leaden vessels holding 16| lb. of the oil. It is invariably sold 
graded on its cimiamic aldehj'^de content, viz., 70 to 75 per cent,, 
75 to 80 per cent., 80 to 85 per cent., and 85 to 90 per cent., the 
usual quahty being 75 to 80 per cent. The lower grades are 
almost invariably adulterated, usually with rosin, pure oils rarely 
containing less than 85 per cent, of cinnamic aldehyde. A pure 
oil (?.e., as distinguished from the oils which may be said to be 
standardised down more or less honestty) has the following 
characters : — 

Specific gravitj’’ 
Refractive index . 
Optica] rotation 
Acid value . 
Cinnamic aldehyde 

— r to + 6° 


Not below 83 per cent. 

A pure oil is soluble in 2 volumes of 80 per cent, alcohol. Nearly 
all adulterants interfere with tliis character. Ordinaiy rosin, or 
coloplionjq the most usual adulterant, can be detected, firstly, by 
a much increased acid value, as colophonj’’ consists almost entirely 
of resin acids or anhydrides ; secondly, bj^ adding a few drops 
of a saturated alcoholic solution of acetate of lead to a 25 per cent, 
solution of the oil in 70 per cent, alcohol. A distinct precipitate 
indicates the presence of rosin. An estimation of the amount of 
the adiilterant is not usually necessary, as the determination of 
the cinnamic aldehyde, upon which the value of the oil practicalty 
entirelj^’ depends, is far more acem-ate than anj^ rosin determina- 
tion. It can, however, be approximately determined by heating 
the oil to 280°, until white fumes are given ofp, when any residue 
above 10 per cent, may be regarded as colophony. Cassia oil 
attacks the lead of the containers, oudng to the presence of 
cinnamic and other acids, Lubetti {Joicr. Soc. OJmn. Ind., 1920, 
35) tests for tliis as follows : 5 c.c. of the oil are dissolved in 
15 c.c. of 90 per cent, alcohol, and this solution “ Nesslerised ” 
against a standard solution of lead acetate in alcohol, with 



sulpliirle of ammonium, using a lead-free cassia oil (redistilled) 
in the blank solution. (For the estimation of the cinnamic 
aldehyde (g.n.), see under “ Aldehydes, Determination of.”) 

Cassia oil closely resembles eimiamon oil in odour, but it is 
not nearly so delicate. Apart from cinnamic aldeltyde, the oil 
contains a little cinnamic acid, terpenes, the acetic esters of 
cinnamic and phenyl-propyl alcohols, or/7m-methyl-coumaric alde- 
hyde, salicylic aldehyde, coumarin, and salicylic and benzoic acids. 

Ca.~sia oil is used in the perfuming of “ old brown Windsor ” 
soap, and in many perfumes where a less delicate odour than that 
of the finer cinnamon oil is permissible. Both oils are frequently 
replaced by artificial cinnamic aldehyde. 

CASSIE.— See » Acacia.” 

CASTOR, or castoreum, is an animal perfume material of 
considerable value to the perfumer as a fixative. It consists of 
the dried membranous follicles of the beaver {Castor fiber), which 
are situated between the anus and genital organs of the animal of 
both sexes. They are fiUed with a viscid oleoresinous glandular 
secretion, which is of disagreeable odour, but which is not noticed 
on dilution. The follicles are removed after the animal is killed, 
and dried either hj smoke or in the sun. When quite fresh, castor 
is a white creamy liquid, but by the time it appears in commerce 
it is unctuous and semi-solid. Two varieties are recognised, the 
Canadian and the Russian, the latter, however, rarely reaching 
tins market. Castor is sold in the form of more or less soft and 
unctuous masses which gradually harden, and which are con- 
tained in flattened and wrinlrled sacs from 2 to 3 inches long. It 
is nauseous as to odour, and of a bitter taste. So far as London 
is concerned, castor comes on to the open market only once a 
year, as it is almost a monopoly of the Hudson’s Bay Companjy 
who offer the year’s collection at an amiual sale, the amount 
ofltered being about 1,000 lb. 

In addition to its direct use as a fixative, castoreum frequently 
enters into the composition of the so-called artificial “ ambers.” 

Castor varies considerably in composition, always, however, 
containing a small quantity of a highly odorous essential oil. It 
contains from 40 to 70 per cent.- of resinous matter soluble in 
alcohol, traces of salicin and benzoic acid, and from 4 to 5 per 
cent, of a crystalline body • which has been named castorin. 
According to Slingard, castor contains 88 per cent, of matter 
soluble in ether, and about 8 per cent, of substances volatile at 

131 0 — 


100°. Castor has frequently been described erroneously as the 
dried testicles of the beaver. 

L3Tin, Lee, and Clausen {Jour. Amor. Pliarm. Ass., 1923, 12, 
419), the leaves of this i)lant, knorvn in the United States as the 
stick}’^ laurel, or mountain balm, jield about 0-1 per cent, of 
essential oil having a specific gravity 1-0167 at 25°, and refractive 
index 1-5315 at 20°. It is optically inactive. It contains cimiamic 
aldehyde, and probabty eugenol. -It has a sweet odour resembling 
cinnamon and clove. 

CEDAR WOOD OIL. — This essential oil is of considerable 
value, mostly for cheap j)erfumery where a heavy odour is 
required. It is distilled from the wood of Juniperus virginimia, 
the Vngmia cedar, with, possibly, the admixtm-e of other cedar- 
woods. Much of it is distilled from the waste shavings obtained 
in the American lead pencil factories. The finety powdered wood 
burns vnth a highl}’’ aromatic odour, and is used in incense and 
similar preparations, and for ceremonial or fumigating pm-poses. 
Although a very inexpensive oil, it is useful in high-grade as well 
as cheap perfumery, and blends well with odours of the violet 
type. The pure oil has a siDecific gravity from 0-940 to 0-9G2, 
and optical rotation — 25° to — 47°. The refractive iirdex varies 
from 1-5000 to 1-5100. The principal constituent of the oil is the 
sesquiterpene cedrene, ; it also contains cedrol, or '' cedar 

camphor,” CigHogO, cedrenol, CjgHg.iO, and ^jseiaZo-cedrol, 
CigHagO. Cedrol is a ci-j’^stalline bodj’’ of pleasant aromatic odour, 
meltmg at 84°. 

The Atlas cedar {Cedriis Atlaniica) is also distilled on a small 
scale for its oil. This tree is probabty only a variety of the cedar 
of Lebanon [Cedrus Lihani). The oil is similar to ordinarj'' cedar 
wood oil, but of finer odour. It has a specific gravity 0-950 to 

0- 970 ; optical rotation, 45° to + 62° ; and refractive index, 

1- 5119 to 1-5175. 

Roberts {Jour. Ghem. Soc., 1916, 791) has examined the oil 
distilled from Cedrus deodara, the deodar tree, a native of the 
western Himalayas, which is widely distributed in northern 
India. The oil has a pleasant balsamic odour, and has the follow- 
ing characters : specific gravity, 0-956 to 0-976 ; optical rotation, 
-f- 34° to -f 62° ; refractive index, 1-5195 to 1-5225 ; and ester 
number, 5 to 21. It contains a ketone, which is probably 
methyltetrahydroacetophenone. Deodar wood oil has recently 




been examined l)y J. L. Simonsen, D.Sc., and M, G. Eau at tlic 
Fore=:t Eesearch Institute, Delira Dun {Indian Forest Records, 
0, 123). The oil einploj'cd by them was derived from logs 
seventy -five yeans old, which furnished a yield of 2'0 per cent, 
of oil. 

The pleasant aromatic odour which characterises deodar oil was 
stated by Roberts to be probably duo to the presence of from about 
2 to 10 per cent, of p-methyltetrahydroacetophcuonc, a compound 
not found previoush' in nature. This statement has been con- 
firmed b}' the above investigators, who worked with a large 
Cjuanlit}’ of the oil, and were thus able to isolate the ketone in a 
pure condition, and establish its identity by preparing many of its 

The principal constituent of the oil is a sesquiterpene, which is 
associated with a sesrpiiterpeno alcohol ; as, however, neither of 
these compounds j'ieldcd a crystalline derivative, it was not 
possible to characterise them beyond determining their physical 
constants. Other constituents which have been isolated from 
deodar oil are as follows : a phenol (unidentified) and esters of 
butyric or isobut^Tic, hexoic, heptoic, and stearic acids. 

Samples of deodar oil were submitted by the Imperial Institute 
in 1915 to English and Continental firms of soap makers and 
essential oil distillers, who expressed the general opinion that a 
market eould probably be found for the oil if it were offered at a 
low price. It was stated concerning a sample of oil which the 
forest chemist has had valued recently in England, that the oil 
might find a small market as a substitute for cedar wood oil in 
soap perfumery, but that its value would onl}’^ be 2s. Gd. per pound. 
At this price it was not considered that production would be 

The suggestion has now been made tliat it might possibly prove 
profitable to utilise the oil obtained by the destructive distillation 
of the wood as a timber preservative. 

A cedar w’ood from East Africa, obtained from Jnniperns 
proccra, has been arriving in Europe for some time past. 3Icssrs. 
ScJiimmcl t& Go. (Bericht, October, 1911, 110) distilled a certain 
quantity of the sawdust and boards of the African wood, and 
obtained the following results : — 

Sawdust. Boards. 

Yield of essential oil . . 3‘2 per cent. . . 3-24 per cent. 

Specific gravity at ] 5° . . 0’9876 .. 1*0289 

Refractive index . . . 1*50893 .. 1*61011 

Optical rotation . . . —37° 10' • . . —32° 30' 



Sawdust. Boards, 

Acid value .... 14*9 . . 27*06 

Ester value . . 8*4 . . 7*93 

Ester value after acetylation . 70*0 . . 89*6 

Solubility in 80 per cent, alcohol 1*6 vol. .. 2 vols. 

Solubility in 90 per cent, alcohol 0*5 vol. . . 0*5 vol. 

CEDRAT OIL. (See “ Citron Oil.”) — The cedrat oil of com- 
merce is almost invariably a roixture of lemon with other Citrus 
oils. The French “oil of cedrat ” is, when pure, citron oil, an 
oil closely resembling lemon oil, having a specific gravity from 
0*850 to 0*855 ; optical rotation, + 77° to -f 83° ; and refractive 
index about 1*4750. It contains citral and terpenes. The French 
“oil of citron ” is oil of lemon. 

CEDRELA WOOD. — Cedi’ela wood must not be confused 
with cedar wood, although its similar odour often causes it to be 
so confused. Cedrela odorata is a native of the Caribbee Islands 
and the Barbadoes. It grows to an immense size in Jamaica. 
The wood has a pleasant cedar-hke odom’, hence it is often called 
Jamaica or Hondm’as cedar. Cigar boxes are usually made from 
tliis wood. It ^fields up to 1 per cent, of a fragrant essential oil 
having a specific gravity 0*923 to 0*950, and refractive index 
1*5040. Similar oils are obtained from the La Plata, Punta 
Arenas, and Corinto cedar or cedrela trees. (S^ E. J. Parry, 
“ The Chemistry of Essential Oils,” 4th ed., vol. i., p. 494.) 

CELERY, OIL OF. — The seeds of the common celeiy, 
Apmm graveoUns, jdeld about 3 per cent, of essential oil, which, 
when distilled from the cultivated plant, is of considerable value 
to the perfumer, both as a fixative and as an addition to floral 
perfumes, such as sweet pea, etc. The oil has a specific gravity 
0*860 to 0*895 ; optical rotation, -f 40° to -f- 82° ; and refraclive 
index, 1*4780 to 1*4860. It owes its odour almost entirely to the 
lactone sedanolide, Ci2lljg02. The oil has been critically examined 
by Ciamician and Silber {Berichte, 1897, 30, 492, 1419). 

CETACEUM. — Cetaceum or spermaceti is a sohd wax ob- 
tained from the head of the sperm whale, Pliysctev 'niacrocsphalus , 
and other allied sea mammalia. It is deposited from the sperm 
oil found in the head of these whales, and is purified by filtration, 
re-melting and treatment with dilute alkali. It has the following 
characters : specific gravity, 0*945 to 0*960 ; acid value, not 
exceeding 1 ; saponification value, 125 to 138 ; iodine value, 3 
to 5 ; melting point, 43° to 50° ; and refractive index about 



1-4330 at 80°. It consists principallj’’ of cetyl palmitate. Adultera- 
tion -with stearic or other fatty acids is indicated h}’’ a Iiigh acid 
value, and, if paraffin vax is present, the sample will not dissolve 
clearh- in 50 to GO parts of boiling alcohol. Spermaceti is used to 
a considerable extent in the preparation of creams and lip salves. 

CHA HAVA. — Tins jdant, a species of GarncUia, is veiy similar 
to the tea plant, hence its name of “ cha hwa,” or tea flower. 
It is largely found in the wild state, flourishing on the slopes and 
summits of the mountains in the jirovince of Che Kiang. The 
chief utilit}'' of tea flower lies in its employment as a scent for 
imparting aroma to the best quality of China tea. Often the 
petals, as well as the entire flowers, are mixed with the tea to 
increase its fragrance, and the resulting mixture, infused in the 
picturesque Cliinese teacups, gives a particularly pleasant 
beverage. Tliis plant also yields a nut, the size of an arachis nut, 
having a brownish colour. These nuts, when subjected to ex- 
pression, 3 'ield a liglit bro'^vn oil, which has a somewhat aromatic 
odour. TJie oil is known locally as Cha Yon, or tea oil, and finds 
extensive use in the coiffure of Chinese ladies. Its cultivation is 
encouraged on this account, and it is especially valuable, being 
easilj’ grown in situations suitable for little else. 

CHAMP AGA FLOWER OIL. — ^This beautiful perfume has 
no relationship with the so-called chamjjaca wood oil (q.v .) , It is 
distilled from the flowers of Miclielia chainqiaca, probabl}'’ usuallj'’ 
mixed ■with the flowers of 3Iichclia loiiqifolia. The former yields 
^mllow, and the latter wliite, flowers. The plants are natives of 
India, and the oil is knowm to the natives as or chainpa-ka- 
‘iiiter and other names. It is, in India , found principally in Nepaxil, 
Assam, and Bengal. It is also cultivated in the Pliilippine Islands. 
The perfume of the flowers is exquisite, but almost overpowering. 
The native Indian women adorn their hair udth the flowers for 
the sake of the perfume and for the rich yeUow-orange colom, 
which contrasts so well with their black hair. The tree is highly 
venerated by the Hindus, who have given one of its names, 
Tulasi, to a sacred grove on the banks of the Yamxma. It is 
also dedicated to the god Vislmu, 

The follo^ving account is diie to Roiire-Berlrand Fils {Bulletin, 
April, 1909, 24) 

“ The tree is kno-wn by different names according to the 
district : Cliampaca, Champaka in Bengal, Tita-sapa in Assam, 
Oulia Gliamp. in Nepaul ; it is also known in other parts of the 



country under the names of Sliav\2>ang, Shimbii, Sempangam, 
Sampige, CliamgmJcam, Saga, Sapu, etc. This large tree, wliich is 
an evergreen, prefers sandy soils. It is of fairlj’’ largo size, since a 
man can scarceh'’ encircle the trunk vith his arms. This trunk 
is gre}^ on the outside, and under the thiclc and greenish-coloured 
bark the wood is nearly white. The branches present the same 
external appearance. The leaves arc not veiy close together ; 
thej" have long petioles, arc oblong in shajic, stiff, greenish brown, 
brilliant above, paler underneath. The nerves are prominent on 
the under -face. 

“ The floAvers, of a 3'elloAv coloiu’, are produced at the tops of 
the branches, and are carried by stout iAcduncles of a j-clloAAnsh 
green coloiu’, polished and erect. The number of flower heads 
ma}’ Amrj’ shghtl^" ; in general there are eight heads to the 
verticillaster. The sepals are rounded at their extremities, the 
petals are cuspidate. The stamens are numerous, the style is 
short and stout. The fruits are on spilces or in bunches, round, 
oblong, pale yellow when ripe. TIica* contain numerous seeds, 
rounded on one face, flattened on the others owing to their 
reciprocal pressure in the fruit. 

“ There are two floAverings annuall}’, and the tree onh* A'iclds 
fruits after some A'ears. 

“ According to om- personal observations, the perfume of the 
flowers of the Philippine chauipaca is stronger and sweeter than 
that of the Singapore, Penang, Colombo and PeradeniA'a floAvers. 
It Avould appear that it is the same AA'ith this tree as AAlth the jdang, 
which does not Aueld the same essential oil in Java, the Straits or 
Ce^don as in the Philippines. It is said that in India the seeds of 
the chamj)aca are 3 *ellow’, whilst in the Philippines the}' arc cheny 

“ The A^ellow coloming matter of the floAvers is utilised in d3*eing. 
The seeds 3'ield a fattj^ oil by pressing ; the flowers contain a 
volatile oil, and 3deld, on distillation, a very pleasant aromatic 
water. All parts of the plant possess a strongly spiced flavour.’’ 

Michclia champaca is generally cultivated, but is found AA'ild 
over a large area. Cultivation greatly improves the perfume. 
The oil has a specific gravit 3 ^ from 0-883 to 0-897, optical rotation 
about — 13°, refractive index about 1-4470 at 30°, and ester 
number about 180. It contains benzyl alcohol, linalol, geraniol, 
esters of meth 3 d-ethyl acetic acid, meth 3 d anthranilate, iso- 
eugenol, benzoic acid, meth 3 d-eugenol, and a cr 3 ^stalline bod 3 ' of 
the formula CigHooC^, melting at 166°. Oil distilled in Manila 



was found by Brooks {Philipp. Jour. Sc., 1911, 6, 333) to have a 
specific gravity at 30730° between 0-904 and 0-9107 ; refractive 
index, 1-4640 to 1-4688 ; and ester number, 124 to 146. An oil 
distilled in the Malay Peninsula had a specific gravity 0-922 ; 
optical rotation, + 12° 30' ; and ester number, 15-2. This oil 
has little odour value. There are several other odorous species of 
Michdia, but they are not used for distillation purposes. Cham- 
paca odour is heavy and persistent, of the same type as ylang- 
jdang and the larger varieties of perfumed lilies. 

GHAMPAGA WOOD OIL.— See “ Bulnesia sarmienti.” 

GHAMPAGOL. — ^This body is a crj’-stalline alcohol jjresent 
in the oil of Bulnesia sarmienti (q.v.). It has been examined by 
Wallach and Tuttle {Annalen, 1894, 279, 395). It has the formula 
CigHggO, and was first named champacol by Merck, when it was 
believed that the wood was true champaca wood, but has been 
renamed guaiol. It is a crystalline body melting at 91°, apd boils 
at 288°. It has a tea rose odour. 

GHASSIS. — ^The name given to the wooden frames, usually 
mth glass bottoms, upon which flowers are treated with fat 
for the extraction of their perfume in the process known as 
enfleurage {q.v.). 

GHAVIBETOL. — This body, also known as betel-phenol, has 
the formida C 10 H 12 O 2 . Chemically it is an. allyl-guaiacol, boifing 
at 255°, of specific gravity 1-069 ; refractive index, 1-5413 ; and 
optical rotation, + 8-5°. 

GHAVIGOL. — ^This body, CgHujO, is a phenol occurring in bay 
and betle oils. It is a highly odorous liquid, of specific gravity 
1-035 ; refractive, index, 1-5441 ; optical rotation, 0° ; and 
boiling point, 237°. Chemically it is para-oxyaUjdbenzene. 

GHEIRANTHUS GHEIRI.— This plant is the wallflower, or 
in France giroflee. It is a perennial plant of the natural order 
Cruciferce, indigenous to southern Europe. The flowers jdeld a 
mere trace of essential oil, so ‘that the natural perfume is not a 
commercial article. Kummert {Ghem. Zeit., 1911, 667) has made 
an exhaustive examination of the oil obtained, to the extent of 
0-06 per cent., by extracting the flowers with a volatile solvent 
and distilling the oil. He found it to have a specific gravity 1-001, 
and a saponification value 20-35. He found present nerol, geraniol, 
linalol, benzyl alcohol, indol, methyl anthranilate, esters of 
salicylic acid, a para-cresol compound, a lactone, and probably 
irone and anisaldehyde. An artificial perfume named cheiranthin 



is compounded on the basis of the above details, and probably 
also contains isoeugenol and isobutyl-phenyl acetate. Hydroxy- 
citronellal and jpam-cresol methyl ether are also employed, 
especial!}^ the latter. 

CHEVREFEUILLE. — A name for honeysuclde perfume {q.v.). 

GHLOROSTYROL. — Styrolene (phenyl-ethylene), CgHg, 
jdelds two sets of halogen derivatives, of which the a 
derivatives are useless in perfumery, but the cu derivatives have a 
powerful hyacinth odour. co-Chlorostyrolene, CgHgCH : CHCl, is 
obtained by the action of caustic allcali on dichlor-ethyl benzene. 
Its odour, however, is not so fine as co-bromostyrolol {vide 
“ Bromostyrol ”). It boils at 198° to 199°. 

CHRYSANTHEMUM OILS. — Clirysantliemxihn marginatum 
(natural order Composiice) is a plant indigenous to Japan, where 
it is known as Isolciku. According to Shinosaki {Jour. Gliem. hid. 
Tokyo, 1919, 22, 455) it jdelds O’ 005 per cent, of essential oil, of 
a gi’eenish blue colour, having the following characters : — 

Specific gravity ..... 0-9231 

Optical rotation . . . . . — 47° 

Refractive index ..... 1’5020 

Saponification value . . . .16-3 

Saponification value after acetylation . 63 

The oil is aromatic, but its constituents have not definitely been 
identified. This oil may be identical with that described by 
Perrier {Bull. Soc. Chim., 1900, iii., 23, 216) under the name kiku 
oil, from Clirysaniliemum J aponicum, although the characters of 
the two oils are different. The flowers of Chrysanthemum cineraria- 
folnim, which provide the insect powders of commerce, jdeld an 
essential oil with a poAverful odour. Its constituents have not 
been completely investigated (Siedler, Berichie Deutsch. Pharm. 
Ges., 1915, 25, 297). 

CHYPRE. — This name is a fancy one, which has become of 
very common application in the perfume industry. It is a perfume 
of heav}^ odour, which is usually based on musk, verbena and 
sandalwood with a little sassafras oil or safrol, with mousse dc 
chCnc or benzoin as a fixative. Clary sage oil is also frequently 
present, and often a little bergamot oil. 

CINEOL. — See “ Eucaljqptol.” 

CINNAMIC ACID.— Cinnamic acid, CgHg.CH : CH.COOH, 
is found, both in the free state and in the form of esters, in various 



essential oils, especially those of balsamic substances such as 
storax. It is a crystalline body, melting at 133°, and boiling at 
300°. It lias a pleasant odour and is useful as a fixative, as tbe 
odour is not too pronounced. It is prepared artificially by beating 
2 parts of benzaldehyde and 3 parts of acetic anhydride Avith 
1 part of fused spdium acetate, to 180° for twelve hours. The 
reaction mass is extracted with water, and the cinnamic acid 
precipitated from the aqueous solution b}’- hydrochloric acid. It 
is also prepared on an industrial scale by heating benzyhdene 
chloride with fused sodium acetate to 200°. 

Claisen {Berichte, 1890, 978) prepares it bj’' treating ethyl 
acetate and sodium with benzoic aldehyde at ice temperature. 
(See also the various cinnamyl esters.) 

Synthetic cinnamic acid is a mixture of two isomeric acids. 
It is composed of an acid identical vdth the natural acid 
(a-cinnamic acid) and a-heterocinnamic acid. 

a-Heterocinnamic acid ma 3 >‘ exist in two forms. In a recent 
paper {Berichte, 42, 2649, 2655), Erlenmeyer has undertaken a 
study of the conditions of formation of these various isomerides 
in nature, and also of the S 5 mthetic cinnamic acids, prepared 
according to the different known methods. These modes of 
formation, which are very numerous, are summarised in a table 
attached to the paper, to which the reader is referred. 

Erlenmeyer first shows that heterocinnamic acid exists, although 
in very small proportions, in the natural cinnamic acid extracted 
from stj'rax benzoin. 

It appears to follow, from a critical examination of the synthetic 
methods which make use of benzaldehyde as their startmg point, 
that, to a large extent, the variations observed in the properties 
of the cinnamic acids obtained shordd be attributed to the influence 
.of impurities in the raw material. 

Thus, natural benzaldehyde, which alw.ays contams a certam 
quantity of hydrocyanic acid, and which gives rise mainly to 
a-cinnamic acid when treated according to Perkin’s method, 
behaves, after all the hydrocyanic acid has been eliminated, like 
the synthetic aldehyde, which yields, under the same treatment, 
storacic acid and the a and modifications of heterocinnamic acid. 
-(See also Campbell and Sudborough, Jour. Ghem. Soc., 95, 1538 ; 
Liebermann and Trucksass, Berichte, 42, 4659, 43, 411 ; and 
Riber and^Goldschmidt, Berichte, 43, 453.) 

CINNAMIC ALCOHOL. — ^This substance, of the formula 
CcHg.CH : CH.CH 2 OH, is also known as styrone. It exists, 



principall}' in the form of its acetic and cinnamic esters, in storax, 
balsam of Peru, and in hyacinth and other floral oils. Much of 
the commercial substance is prepared by the hydrolysis of the 
cmnamic esters present in storax. It is prepared' artificially by 
reducing cinnamic aldehyde diacetate by means of iron and 
acetic acid, and saponifjdng the resulting esters. It is a crystalline 
bodj^, melting at 30'* to 33°, but commercial specimens almost 
invariably contain traces of impurities which keep it in a liquid 
condition. It has a specific gravity about 1*020 (commercial 
specimens vary from 1*015 to 1*030) ; refractive index, 1*5720 at 
30° ; and boiling point, 258°. The odom- of cinnamic alcohol is 
weak, but very sweet and delicate. It is useful in the preparation 
of artificial h 3 ’-acmth and snnilar floral odours, 

CINNAMIC ALDEHYDE. — ^This aldehj’de is the principal 
odorous constituent of cinnamon and cassia oils. Its formula is 
CcHg.CH : CH.CHO. It can be extracted from the oils in which 
it occurs by shaking it with a hot solution of sodium bisulpliite, 
which combines with the aldehj^de to form a soluble compound. 
The aqueous solution is separated from the non-aldehj’-dic con- 
stituents, which float on the surface of the liquid as an .oil, and 
on the addition of dilute sulphuric acid the aldehyde is liberated 
from the bisulphite compound, and can be distilled in a current of 

Cimiamic aldehj^de is prepared on a comparatively large scale 
by condensing benzaldehj’-de vdth acetic aldehj^de in the jpresence 
of an alkali. This method, originaUj'- due to Boehringer (German 
Patent 19018), is as follows : A solution of 5 parts of benzaldehyde 
and 5 parts of acetic aldelij’-de in 10 parts of alcohol is cooled to 
10°, and 10 parts of a 25 per cent, solution of caustic soda solution 
in water are gradual^ added, the addition taking from five to ten 
minutes. The temperature should not be allowed to rise. When 
the liquid is cpiite transparent, it is allowed to stand for twent}*- 
minutes, and is then poured into an excess of water. The separated 
cinnamic aldehj^de is purified by rectification. For perfumery 
purposes cinnamic aldehj^de should be free from chlorine. 

Pure cinnamic aldehyde should have a specific gravit}'- from 
1*054 to 1*057 ; optical rotation, 0° ; refractive index, 1*6195 ; 
and boiling point, 253°. 

It is employed to a considerable extent where a powerful 
ciimamon odour is required without the delicacy of the natural 
product. It is also used in the preparation of an artificial oil of 
cinnamon. {Vide “ Cinnamon.”) 





CINNAMON, — ^Tlie odour of cinnamon has from time 
immemorial been highly appreciated by the perfumer. The 
principal products of odour value are : the essential oil distilled from 
the bark, ■wdiich is the ciimamon oil, properly so called, of com- 
merce ; and the essential oil distilled from the leaves, valued as a 
soiu’ce of eugenol. A good deal of the oil of cinnamon distilled in 
Ceylon is, in fact, a mixture of bark and leaf oil. 

The plant yielding these products is Ginnamoniwn zeylanicum, 
a native of Cejdon, found in moist low country up to an elevation 
of about 2,000 feet. The tree is also grown in India, Mauritius, 
the Seychelles, and Jamaica, but the greater part of the world’s 
supply is derived from Ceylon. It has been stated to occur wild 
^ in the Malay Peninsula, but according to H. N. Ridley, the 
Director of the Botanic Gardens, Straits Settlements, this is 
doubtful. He has found the allied tree Cinnamomum inero there, 
and whilst it is almost impossible to detect any botanical differ- 
ences between tins tree and the Ceylon cinnamon, the taste and 
odour of the barks are quite different. He considers it probable 
that the true Ceylon cinnamon is a very aromatic form of C. inero. 
It is probable that the cinnamon mentioned in early writings 
was in fact cassia, which was certainly imported into Arabia 
from China in very early days. 

In the sixteenth century Ceylon cinnamon was entirely derived 
from wild trees, and the collection of the bark was controlled by 
the Portuguese, who had occupied the island in 1536. About 
100 years later the Dutch took the island, and in 1770 De Koke 
commenced the cultivation of the tree, and the Dutch obtained 
about 200 tons of bark annually, burning the bark when supplies 
were excessive in order to keep the price up. 

"The “ cinnamon gardens ” of Ceylon are situated principally 
in the south-west of the island. The bark is exported either in 
the form of pipes or quills, or in the form of chips or small frag- 
ments, the latter being used for the distillation of the essential 
oil. The oil distilled in Ceylon is usually obtained by macerating 
the chips in brine for a few days and then subjecting them to 
distillation. The yield varies from 0-5 to 1 per cent. A con- 
siderable amount of the bark is distilled with the addition of 



leaves, or cinnamon leaf oil is added to tlie oil distilled from tlie 
bark. In purchasing Ceylon distilled oil it is necessary to examine 
the product from this point of view, as the leaf oil has none of the 
characteristic cinnamon odom’, but closely resembles clove oil. 

The oil of ciimamon bark owes its odour to its principal con- 
stituent, cinnamic aldehyde {q.v.), but, of course, modified by the 
presence of secondar}’- constituents. The characters of the oil 
depend on the condition of the raw material, and also on the 
method of distillation employed. The oil distilled on the Continent 
generally possesses a higher specific gravity than that distilled 
in England, and that distilled in the Seychelles differs very 
considerably from all other bark oils. The following figures are 
given by E. J. Parry (” Chemistrjr of Essential Oils,” 4th ed.,* 
vol. i.) : — 

English distilled. 1 

Continental dis- 

Seychelles oils. 

Specific grawty . 




Optical rotation . 

0° to — 1° 

0° to — 1° 

1 — l°to— 3° 

Eefractive index . 



1 1-5280-1-5335 

Cinnamic aldehyde 

58-70 per cent. 

63-76 per cent. 

25-36 percent. 


Ce 3 don cinnamon bark oil contains, in addition to cinnamic 
aldehj^de, the following bodies : methjd-amyl ketone, pinene, 
phellandrene, cymene, benzaldeh 5 ’-de, nonylic aldehj^de, eumic 
aldehyde, linalol, finalyl isobutyrate, eugenol, and caryoplij^Uene. 

Cinnamom leaf oil is entirely different from the bark oil. It 
consists mamly of eugenol (up to 95 per cent.), which can be 
extracted and used for the manufacture of vanillin. This oil has 
a specific gravity from 1-040 to 1-065 ; optical rotation, — 0° 10' 
to -|- 2° 35' ; refractive index, 1-5300 to 1-5450 ; and eugenol 
value, 70 to 95 per cent. 

It has been stated that Madagascar cinnamon leaf oil contains 
a considerable amount of benzyl benzoate. This requires con- 
firmation, but the eugenol in this oil should be determined in 
the cold, as otherwise benzyl benzoate is decomposed and inter- 
feres with the accuracj- of the determination. 

Samples of cinnamon bark oil from the Gold Coast have been 
examined at the Imperial Institute. Three samples' were reported 
upon in the Bull. Imp. Inst., 1919, V7, 189, and compared with a 
sample previously reported upon {ibid., 1918, 16, 146). 



The three samples were as follows : — 

No. 1. From Assiiant^i . — ^This eonsisted of pieces of rolled 
hark, of pale reddish bro-rni colour, about 10 inches in length and 
1 inch in uddth. The roUs were very irregidar in shape, and much 
scarred and tom. 

The aroma of tliis material was inferior to that of Ceylon 
cinnamon bark. 

No. 2. From Cooma-ssie . — ^This sample consisted of rolls of bark 
measming 12 inches in length and 1 to 1^- inches in width. The 
material resembled sample No. 1, but possessed a better aroma. 

No. 3. From Ahuri . — ^This bark v'as in rolls about 91 inches long 
and f inch wide. It was similar in appearance to sample No. 1, 
though somewhat paler, wliilst the aroma was more fragrant than 
that of sample No. 1, but not equal to that of sample No. 2. 

Distillation trials were carried out with the tliree barks at the 
Imperial Institute in order to deterniine the yields of volatile oil 
which they furnished, and the results are shown below in com- 
parison with the corresponding figures for the previous sample 
from Tarquah referred to above : — 

No. 1 


No. 2 


No. 3 
fro m i 

No. 4 

“ Heavj’’ ” oil which sepa- 
rated from the aqueous 

Por cent. 

Per cent. 


Per cent. 

Per cent. 


“Light” oil extracted with 
ether from the aqueous 





distillate .... 


0 3 

0 30 

Total yield of oil 





1 48 

It will be seen that the jdelds of oil from the later samples are 
somewhat higher than that fui-nished hj the original sample from 
Tarquah. They are also considerably in excess of those yielded 
by Ceylon cinnamon bark, which vary from 0-5 to 1 per cent. 
The samples had the following characters : — 


1 . 




Specific gravity 





Refractive index 






74 per cent. 

88 per cent. 

86 per cent. 

86 per cent. 



Roiire-Berlrcnid Fils [Bulletin, October, 1920, 36) have examined 
a cimiamon oil from Amiam, wliicli had the following characters : — 

Specific gravity ..... 1-051 

Refractive index at 17° . . . 1-6090 

Optical ]’otation . . . . . — 0° 8' 

Acid value . . . . .2-8 

Aldehydes 95 per cent. 

The root bark yields an essential oil, but it is not an article of 

A Japanese plant, Cinnamomum Lozireirii, jdelds an essential 
oil which contains about 25 to 30 per cent, of cinnamic aldehyde. 

Cinnamomum glan chili ferum (or G. Cecioclaplme ?), the Nepal 
sassafras tree, is highly odorous, and its leaves jfield an essential 
oil, which, however, contains httle, if any, cinnamic aldehyde. 

Culilavan oil is the product of the bark of Cinnamomum 
Culelaicau. It contains about 60 per cent, of eugcnol and some- 
what resembles ordinaiy cinnamon leaf oil. 

The so-callcd Brisbane “ white sassafras ” is Cinnamomum 
Oliveri. Its bark vfields an essential oil containing phenols, but no 
cinnamic aldehyde. 

The exports of cinnamon bark (apart from oil) from Ceylon 
amount to between 2,000,000 and 3,000,000 lb. per annum. 

For details of the cultivation of cinnamon, its diseases, and the 
preparation of the bark for export, see “ Spices,” by H. N. Ridley 
(Macmillan & Co., Ltd., London). 

CINNAMEINE. — ^This name is used loosely to signify the 
mixture of benzyl benzoate and cinnamate present in balsam of 
Peru, etc. Strictly, it is sjmoiymous vith benzyl cinnamate [q.v.). 

CINNAMYL ACETATE.— This ester has a sweet floral 
odour. It has a specific gravity 1-0184, refractive index 1-5295, 
and boils at 262°. 

CINNAMYL BUTYRATE. — ^This ester, of the formula 
CcHg.CH : CH.CH2.C02(C3H7), has a fine fruity odour. It must be 
used in very small quantities. It is prepared bj’- the esterification 
of cinnamic alcohol and but^rric acid. It has a specific gravity 
1-023, and refractive index 1-5255. 

CINNAMYL CINNAMATE. — ^This ester, knovm also as 
st3T:acin, occurs naturally in storax and other balsamic substances, 
and probabty, in traces, in essential oil of hyacinth. It is also 
prepared artificially b^’' the esterification of the alcohol and the 
acid. It forms a crystalline mass melting at 44°. It has a sweet 



heavy odour resembling that of balsam of Peru. Its formula is 

• CH.CHo-COj.CH : CII.CgH 5 . Its specific gravity is 
1-040 at 25°. 

^ GINNAMYL PROPIONATE. — ^Tho odour of this ester, 

• GII.CH 2 .C 02 (C 2 Hg), resembles that of grapes j it is 
used in the manufacture of fruit and floral odours. 

CISTUS CRETIGUS. — See “ Labdanum.” 

GITRAL.— Citral, or geranaldohyde, CioHigO, is an aldehyde, 
or, more properl}’', a mixture of t'wo isomeric aldeh 5 ’'des, and is 
the characteristic odour bearer of lemon oil, lemongrass oil, true 
verbena oil, and the oil of Baclchoiima citriodora, in each case 
modified by the presence of subsidiary constituents. Citral as a 
commercial article is practically entirely extracted from lemon- 
giass oil, as, on account of price, the oil of Backliousia is unable 
to compete. It occurs in numerous essential oils, and may be 
obtained by the oxidation of geraniol, nerol, and linalol. Com- 
mercially it is extracted from lemongrass oil, previously fraction- 
ated, in the form of its bisulphite compound, from which, after 
pressing and draining, it is removed by decomposition with a 
dilute acid and distillation with steam. Thus, prepared com- 
mercial citral is a pale yellow oil with an intense lemongrass odom* 
— so powerful that, after smelling it, the nose is frequently 
paralysed and unable to smell anytliing else for some hours. It 
is a mixture of a-citral or geranial and /3 -citral or neral. The 
commercial mixture and the two isomers have the foUo'wino' 
characters : — ° 


a -Citral. 


Specific gravity at 20° 




Refractive index . 




Boiling point at 20 mm. . 




The principal importance of citral to the perfumer is the fact 
that it is the sole raw material from winch ionone and similar 
artificial violet perfume materials can be manufactured. As such, 
citral is only used to a small extent in perfumes, but in certain 
cases it imparts as harp odour to floral bouquets which is much 
appreciated. (For the conversion of citral into 'ionone, vide 
“ Ionone.” For the determination of citral, see “ Aldehydes, 
Determination of,” and “ Lemon, Oil of.”) 




GITRAPTENE. — ^Tliis substance is the main constituent of 
the non-volatile residue of lemon oil. Its formula is CuHioO^, 
and its melting point 146° to 147°. It is a dimethoxy-coumarin. 

CITRON OIL.— See “ Cedrat Od.” 

^ GITRONELLA OILS. — There are two main tj^pes of these 
oils, namelj’", “ Ceylon ” and “ Java.” Oil of the former tj’pe is 
produced chiefly in Ceylon, while oil of the latter tj'pe is produced 
in Java, Federated Malay States, and Burma. 

The Ceylon type is distilled from the grass Cywhopogon Nardus, 
Rendle (Lenabatu grass) {Bull. Imp. Inst., 9 , 1911, 240, 333 ), 
while the Java type is distilled from the grass Cynihopogon 
Winisrianus (Maha Pengiri grass) {K&w Bulletin, 1906, 8 , 297).' 
Both types of oil are chiefly used for perfumery purposes, and 
mainly in the soap industry. 

Ceylon Citronella Oil.— This t 3 rpe is almost entirely distilled 
from grass cultivated in south Ceylon, although small quantities 
are also produced in the Seychelles and the island of Mayotte. 

The exports of this oil from Ceylon for the 5 'ear 1922 were 
1,325,355 lb., and for 1923 they amounted to 1,118,619 lb. Of 
these the United Kingdom took 313,403 lb. in 1922, and 379,200 lb. 
in 1923 ; while the United States took 779,951 lb. in 1922, and 
571,841 lb. in 1923 {SchimmeVs Bericlit, 1924, p. 14). 

The oil is distilled by natives in qmte primitive stills, which 
produce about 25 lb. of oil per day, the yield of oil being 0*5 to 
1 per cent, of the grass. 

Practically all the Ceylon citronella oil that is dealt in com- 
mercially is adulterated with a small quantity of kerosene, 
although a pure grade is obtainable under the description of 
“ estate oil.” 

In order to restrict the amount of adulteration, a test was 
dev sed by Messrs. Scliimmel, and this test has long been known 
as ‘ Schimmel’s test,” and is sometimes incorporated in com- 
mercial contracts, wliich set out that the oil sold is “ guaranteed 
to pass Schiramel’s test.” 

This is purely a solubiHty test, and depends on the relative 
insolubility of kerosene in 80 per cent, alcohol. It was soon 
found, however, that it was not capable of detecting the presence 
of less than 5 per cent, of kerosene, and I\Iessrs. Scliimmel, there- 
fore,^ mtroduced a further test, which they caled the ‘‘raised 
test, but it has not come into general use in England or the 
United States. 



Messrs. Scliimmers iastructions (SchimmeVs Bericht, 1923, p. 18) 
for caiTjang out these tests are as follows : — 

Schimmd's Test . — Citronella Oil shall be soluble to a clear 
solution in 1 or 2 volumes of 80 per cent, alcohol (specific gravity, 
0-8642 at 15° C.). This solution, on addition of further volumes 
of 80 per cent, alcohol, shall become not more than slightly 
opalescent and show no marked turbidity. The alcohol shall be 
added gradually, and if a turbiditj’^ does develop, further alcohol 
is added until the turbidity reaches a maximum. When the 
maximum turbidity is obtained, the solution is carefully examined 
to see whether any oil3’' droplets have separated out. If no 
separation of oily droplets is shown, the oil is said “ to pass 
Schimmel’s test.” 

In no case must more than 10 volumes of alcohol be 
used, and the oil and alcohol mixture should not be violently 
shaken, as otherwise the oilj'' droplets may become too finely 

In England (P. dk. E. 0. R., June, 1923, p. 179, vol. xiv.. No. 6) 
tliis test is often carried out in a slightlj’’ different manner ; 
instead of the 80 per cent, alcohol being added gradually, 10 
volumes of 80 per cent, alcohol are added to 1 volume of Cejdon 
citronella oil ; tliis mixture is shaken and allowed to stand for 
tw-enty-four hours, after which time no oily droplets should have 

Schmimel’s Raised Test . — ^To the original oil 5 per cent, by 
volume of petroleum is added, and this mixture is then tested by 
the ordinary Schimmel’s test. 

Both these tests are purely empirical, and, while easj’’ and 
convenient to carry out, are by no means conclusive proof as to 
the purity of the oil or the extent of the adulteration. 

In 1923 large quantities of citronella oil were shipped to America 
and England which “ passed Schimmel’s test,” but these oils were 
even more heavily adulterated vdth kerosene than usual ; in 
order, however,’ to cover the adulteration, alcohol had been added 
to the oils so that they should pass Scliimmel’s test, and in some 
cases the amount of alcohol that had been added amounted to 
20 per cent. 

When these oils were washed with three times their volume of 
1 per cent, sulphuric acid, which removed the alcohol, the washed 
oils no longer passed Schimmel’s test, and both the specific gravity 
and refractive index of the washed oils were materially higher 
than those of the unwashed oils. 


10 -a 


A pui’e Ce3don citroiiella oil known commercially as “ estate 
citronella oil ” has the following characters : — 

Specific gravity at 15-5° C. 
Oj)tical rotation 

Refractive index at 20° G. . 
Acetyli sable contents (as geraniol) 
Solubility in 80 per cent, alcohol . 


— 7° to — 18° (usually 
about — 12°). 


GO per cent.-G3 per cent. 

1 in H volume, and 
passes both Schimmel’s 
Test and Schimmel’s 
Raised Test. 

On distillation, no fraction should distil below 1G0°C. (absence 
of alcohol and light pcti’oleum). 

The first 10 per cent, distilled under reduced pressure (20 to 
40 mm.) must have a specific gra%uty not below 0*858, and a 
refractive index at 20° C. not below 1*457 (Parry’s “ Chemistry of 
Essential Oils,” 4th ed., vol. i., p. GG). 

When washed with three times its volume of 1 per cent, sulphuric 
acid, the refractive index of the washed oil should not show an 
increase of more than 0*0005 at 20° C. (absence of alcohol). 

The characters of tlie usual commercial quality of Ceylon 
citronella oil, and which oil is sold under the description “ Cejdon 
citronella oil passing Schimmers test,” are as follows : — 

Specific gravity at 15*5° C. . 

Optical rotation 

Refractive mdex at 20 ° C. . 

Acetyhsable contents (as geraniol) 
Solubihty in 80 per cent, alcohol . 

0*895-0*910 (usually not 
less than 0*900). 

— 7° to — 18° (usually 
about — 12°). 

1*479-1*485 (usuall}’’ not 
less than 1*4815). 

55 per cent.-5S per cent. 

1 in l^- volume, and 
passes Schimmel’s test. 

When washed with three times its volume of 1 per cent, sulphuric 
acid, the refractive index of the washed oil should not show an 
increase of more than 0*0005 at 20° C. 

This oil is distinguished from pure Cejdon citronella oil by — ^ 

(1) Its lower content of acetyhsable constituents. 

(2) It usuaU}’- does not pass Schimmel’s raised test. - 

(3) The lower specific gravity and refractive index of the first 
10 per cent, distilled under reduced pressure (Parry’s “ Chemistry 
of Essential Oils,” 4th. ed., vol. i., pp. G5-GG). 

Parry and Bennett have fractionated samples of genuine Ceylon 
citronella oil, samples adulterated with definite amounts of 



petroleum and resin spirits, and samples of the usual market 
quality of Ceylon eitronella oils, and find the characters of the 
first 10 per cent, distilled from the oil to be as follows : — 

Pure CifroncUa Oils 

Specific cravitv at 

15 >C. * 

Rotation in 100 mm. 

Refractive index at 
19° C. 



— 44° 




- 43° 



O-SGO ; 

- 35° 



0-SG3 ! 

- 23° 



-0-SGG j 

— G° 




- 11° 


Gilroneila Oils mixed with AduKeranis 

gravity at 

in 100 mm. 

index at 

10° G. 

1 E + 5 

iier cent, resin spirit 



2 E + 10 




3 E + 15 

/J 31 ! 



4 E d- 20 

33 33 i 



5 D -f 5 

M 33 


- 17° 


6 D -f 10 

33 33 


- 14° 


7 D + 20 

33 33 



8 C + 10 

per cent, iictroleum 
spirit , 




Adidieraicd Citronella Oils on the Market 

Specific gravitj” at 
15-5° C. 

Rotation in 100 mm, 

Refractive index at 
19° C. 



— 26° 48' 



— 23° 50' 



— 18° 20' 



— 22° 











— 29° 




Resin and Pcirolenm Spirits 


! ^Specific 
giavily at 



j Potation 

1 in lOO nnn, 
i tube. 

index at 

10° C. 

1, Eesin spirit . 


+ 4° 


9 ' 


+ 2° 30' 


3. Petroleum spirit (tur- i 
pentinc substitute) . ' 


+ 1° 


4. 1 


+ 1° 30' 


Tlie lightest fraction wliicli Parrj’’ and Bennett obtained from the 
adulterated oils had a specific gravity of 0-79S, an ojjtical rotation of 
— 17°, and commenced to distil at 112° C. In none of the fractions 
was any pronounced odour observed, nor any fluorescence ; hence 
the conclusion that resin spirit is the adulterant. 

The acctylisable constituents of Ceylon citroncUa oil consist 
in the main of a mixture of geraniol and citronellal. in which the 
geraniol predominates, although small amounts of acctylisable 
compounds, such as borncol, etc,, have also been identified. 

Regarduig the proportion of geraniol to citronellal, Messrs, 
(Schimmel {SclihnmcVs Rej^orl, April, 1923, 44, and April, 1914, 

p. 44) have examined five samjilcs of Ce 3 don citroncllo oil, with the 
following results : — 





1 Rotation. 










j Citronellal. 



' Klobcr’s 
j Jlothod, 

1 Piicn}'!- 
1 liydrazino. 




Per rent. 

Per cent. 


Per cent. 

Por cent. 


— 11° 22' 






— 11° 28' 






— 11° 40' 






— 11° 43' 






— 11° 31' 





From these and the values previously obtained, Messrs. 
Schimmel set out the following limits : — 

Per cent. 

Geraniol ..... 29-6-34-4 

Citronellal (Kleber) . . . 7* 5-1 1-6 


Citronellal (Dupont) . . .6-6- S'O 



A critical examination of the chemical constituents of a pure 
sample of Ceylon citronclla oil carried out by Messrs. Schimmel 
{SchimmeVs Rcporl, April, 1912, p. 44) resulted in tlio presence of 
the following compounds being identified ; citronellal, camphene, 
dipentene, borncol, gcraniol, methyl-heptenone, methyl-eugenoli 
esters of valeric acid, a tcrpene of very low specific gravity, a 
body related to linalol, thujono, ncrol, d-citronellol in the 
form of acetic and but\Tic esters, gcranyl acetate, and a high 
boiling Irevorotatory h.ydrocarbon C 13 H 0 ,. 

Ja^-a Citronella Oil.— This oil is chiefly produced in Java, 
although an increasing amount is now also produced in Burma 
and the Federated Malay States (“ JIalay Citronclla Oil ” P <£? 
E. 0. R., vol. XV., No. 4, p. 120). 

For the 3 'car 1921 Java e.xported {SchiinincVs Ecricht, 1924, 
p. 17) 273,140 kg., but in 1922 this rose to 434,708 kg. 

Of these quantities, 13,052 kg. and 137,944 kg. were exported 
to England for 1921 and 1922 respectively, while to the United 
States the exports amounted to 100,931 kg. for 1921 and 
97,900 kg. for 1922. 

In Java {SchimmeVs BericM, 1924, p. 17) the oU is distilled 
from the fresh grass, the grass being cut after the first six months, 
and then every four months for a period of four years, after which 
the plants must be replaced. There are approximate!}'- 15,000 
acres in cultivation, and the 3 neld of oil is 50 to GO lb. per acre 

per 3 'ear, and there are thirty-five factories employed in distilling 
the grass. ° 

The characters of the oil produced in Java and Malay are practi- 
call}' identical, but those of Bunnese oil are somewhat different. 

All these oils differ materially from that of the Ceylon t 3 'pe, 
not only in odour, but also in physical and chemical charactei’s, 
their main difference being much higher contents of citronellal 
and total acet 3 disable contents. 

These oils are sold on the basis of their acet 3 disable con- 
stituents, those from Java and Malay being usually bought on a 
basis of not less than 85 per cent. acot 3 'lisable constituents 
calculated as gcraniol, while for the Burmese oil an acetylisable 
content of 90 per cent, is often stipulated. 

These oils are not often adulterated, and rarely suffer the gross 
adulteration that is common to Ce 3 don citronella, although at 
intervals they suffer adulteration with fatty oils {P. & E. 0 R 
July, 1923, vol. xiv.. No. 7, p. 254), and Messrs. Schimmel have 
examined two samples adulterated with motor spirit. 



The characters of the oil produced in Java and the Federated 
Malay States are as follows : — 

Specific gravity at 15-5° 0. 
Optical rotation 

Eefractive index at 20° C. 

Acet 3 disahle contents (as geraniol) 

Non-volatile residue at 100° C. ^ 
Solubility in 80 per cent, alcohol ^ 

0- 885-0-895 

0° to —3° (rarely 
slightly +). 

1- 460-1-472 (seldom 

less than 1*468). 

80 per cent, to 92 per 
cent, (usually not 
less than 85 per cent.) 

1*5 per cent, to 5 per 

1 in 2 volumes, and Ire- 
coming not more 
than slightly opales- 
cent in 10 volumes. 

When washed with three times its volume of 1 per cent, sulphuric 
acid, the refractive index of the washed oil should not show an 
increase of more than 0*0005 at 20 C. (absence of alcohol), and 
as a rule the refractive index of the washed oil is slightly lower 
(up to 0*001) than that of the original oil. 

Not more than 24- per cent, should distil below 208° C. 

The acetjdisable constituents of Java citronella oil consist, in 
the main, of a mixture of geraniol and citronellal, in which the 
citroneUal predominates. 

Messrs. Scliimmel {ScJiimmeVs Ee^Jort, April, 1913, p. 44, and 
April, 1914, p. 44) have examined seven samples with special 
reference to their geraniol and citronellal contents, and give the 

folloving figures : — 



1 Rotation. 






1 Citronellal. 





Per cent- 

Per cent. 1 

Per cent. 

Per cent. 


— 2° 15' 






- 1° 45' 



- 40*0 



— 1° 35' 






— 1° 22' 






— 1° 28' 






— 2° 11' 






— 1° 11' 





1 P. tk E. 0. B., July, 1923, p. 254, vol. xiv.. No. 7. 


From these and previous results they suggest the following 
limits : — 

Per cent. 

Geraniol . . . . . 26-G 40-1 

, Citroncllal (Kleher) . . . 35-41 


Citroncllal (Dupont) . . . 35-4G 

Oils produced in Burma usually have the following characters : — 

Specific gravity at 15'5° C. . . 0'890-0-n00. 

Optical rotation . , . . 0 to 2° (very rarel^f 

slightlj’ — ). 

Eefractivc index at 20° C. . . l*4G9-l-472. 

Acetj'lisable contents (as geraniol) 89 per cent, to 93 per 


Non-volatile residue at 100° C. ^ .2 per cent, to 5 per 


Solubility in 80 per cent, alcohol ^ . 1 in 2 volumes, becom- 

ing not more than 
opalescent in 10 vols. 

As in Java citronclla oil, the acetylisable constituents of Burma 
citronella oil consist in the main of a mixture of geraniol and 
citroncllal, but the amount of geraniol iwcsent is.usuallj’’ somewhat 
higher than that found in Java citronclla oil, and often amounts 
to 50 per cent, of the oil, 

Burma citronella oil is, as a rule, distinguished from that 
produced in Java by — 

(a) The optical rotation of the Burma oil is usuall}’’ to the right, 
wliile tliat of the Java is almost invariabl}’^ to the left. 

(&) The refractive index and specific gravity of the Burma 
oil are relatively higher for the same total acet 3 disable contents 
than those of the Java oU. 

In the case of Burma citronella oil a specific gravity of 0-893 
would indicate an acetylisable content of about 92 per cent., 
wliile for an acetylisable content of 90 per cent, the specific 
gravity would be about 0-89G. In Java oil a specific gravity of 
0-893 is usually found, together vith an acetylisable content of 
about 8G per cent., while for an acetylisable content of 90 jier 
cent, the specific gravity would be about 0-888. 

Fm'ther references to citronella oil : — 

“ Separation and Detection of Benzine and Petroleum ” (Dodge, 
Eighth International Congress of Applied Chemistry, 1912, vol. vi., 
p. 8G). 

1 P. & E. 0. It., July, 1923, p. 264, vol. xiv.. No. 7. 



'‘Anatysis of Oil of Citronolla ” (P. dh E. 0. R., June, 1913, 
voL iv., No. C), p. 107). 

Effect of Climate on Burma Citronella Oil ” (P. c& E. 0. R., 
Tol. T., No. 12, p. 398). 

“ Some Abnormal Samples of Java Citronella Oil ” (P. <b 
E. 0. R., vol. V., No. 8, p. 275). 

“ Formosan Citronella Oil ” (P. cb E. 0. R., vol. yii., No. 9, 
p. 279 ; vol. ix., No. 13, p. 323 ; vol. x., No. 10, p. 240). 

“ Specific Gravity of Ceylon Citronolla Oil at Temperatui’cs 
from 15° to 35° C.” {SchimincVs BericJii, 1923, p. 19). 

“ Viscosity of Java Citronella Oil ” {ScJmnmcl’s B&richt, 1924, 

CITRONELLAL. — Commercial cilroncllal is, according to the 
latest researches, like citral, a mixture of two isomeric aldehydes, 
of the formula CjoHigO. Of these the isomer corre.sponding with 
citroncllol is citroncllal, and that corresponding with rhodinol is 
termed rhodinal. Citroncllal is the chai'act eristic odour bearer 
in Java citronella oil, and also in Ceylon citronella oil ; in both 
oils it is mixed with gcraniol, the citroncllal predominating in the 
former, and the gcraniol in the latter oil. Citroncllal is extracted 
from citronella oil by means of its bisulphite compound in the 
same wa.y as citral is prepared. The oil is fractionated and the 
gcraniol recovered b^’’ means of its calcium chloride compound, 
or by other suitable means, so that practically the whole of the 
two constituents is recovered. 

Citroncllal has a penetrating odour, but is only suitable for cheap 
perfumery. It is, however, the raw material for the manufacture 
of h 3 xlrox 3 ’'-citronellal {q.v.). 

Commercial citroncllal is a pale 3 ^cUow or colom-lcss oil having 
the following characters ; boiling point, 205° to 208° ; specific 
gravity, 0-855 to 0-858 ; refractive index, 1-4450 to 1-4480 ; 
optical rotation, + 9° to -}- 12°, occasionally slight^’- Irevo- 
rotator 3 ’’if prepared from Java oil. Brins {Chem. ceJcMacl , 1917, 
14, G92) gives the following characters for the isomers of 
citroncllal (assuming the usuall 3 ^ accepted constitutions of 
citronellol and rhodinol are correct) : Citroncllal — specific gravity, 
0-888 at 14° ; boiling point, 203° to 204° ; and melting point of 
scmi-carbazone, 85° to 80°. Rhodinal — specific gravity, 0-8745 
at 14° ; boiling point, 198° to 199° ; and melting point of semi- 
carbazonc, 83° to 84°. 

Pure citroncllal is usually obtained b 3 ^ extracting the unchanged 



citroiiellal in the manufacture of citronellol from citronella oil 
by means of sodium bisulphite. 

CITRONELLOL. — Citronellol CjoHoqO is an alcohol found in 
rose, geranium, and other essential oils. An acute controversy 
-has for many years raged over the question of the relationships 
between geraniol, citronellol and rhodinol. Ehodinol was put 
xipon the market as a specific chemical individual diffeiing from 
both geraniol and citronellol, by Ereneh chemists (Barbier and 
Bouveault) ; various German chemists insisted that it was merely 
a mixture of the other two alread 3 ’' well-knovTi alcohols. Bodies 
named roseol and reuniol then appeared, but the most recent 
work of Barbier and Loequin {Comptes Remind, 157, 1114) and 
Harries and Comberg {Annahn, 1915, 410, 1) has praetically 
settled the question, and roseol and reuniol, as well, probabl}'-, as 
commercial rhodinol, m.a}’- be regarded as impure bodies. Com- 
mercial rhodinol, however, has been shovm to contain an isomer of 
citronellol, for which the name rhodinol has been retained. It 
maj’- be taken for granted, therefore, that both citronellol and 
rhodinol, as met vdth in commerce, are mixtures of the two 
isomers. The following arc the characters of the commercial 
articles which are usually obtained from citronellal bj’’ reduction, 
and from geranium oil : — 

From geranium oil, 

Boiling point at 17 mm. . — 

Boilmgpointat764mm. . 225°-22G° 

Specific gravity . . 0'SG2 

Refractive index . . 1’4570 

Optical rotation . . — 1° 40' 

Prom citronellal. 


+ 4° 

Citronellol and rhodinol have faint but sweet rose odours, 
and are used in the preparation of artificial otto of rose, where 
it is usually associated with geraniol, phen 3 d-cth 3 d alcohol, oct 3 d 
alcohol, dec 3 ’'l and nonyl aldeh 3 ’-des, traces of citral and traces 
of phenyl-acetic acid, and various esters of geraniol and citronellol. 
(See also “ Rhodinol.”) 

The following is the usual method for the preparation of 
citronellol by reduction of citronellal (Lewinsohn, P, ds E. 0. R., 
1923, 360) 

Ten kilograms of aluminium turnings freed from grease by 
washing in petroleum ether are treated with caustic soda solution, 
and when hydrogen is briskly evolved the caustic solution is run 
off and the metal washed with water. It is then treated for a 
short time with 1 per cent, solution of mercuric cldoride. To 



9*3 kg. of aluminium so treated 54 kg. of 80 per cent, alcoliol and 
18 kg. of citronellal are added, and then 0*45 kg. of mercuric 
chloride. Eeaction commences at once, and the temperature must 
he kept down to 35° by vigorous stirring and, if necessary, a water 
jacket. The reaction mass, after sixteen hours, is diluted with 
water and filtered, and then distilled, traces of citronellal being 
removed from the citronellol by treatment with sodium bisulphite. 

GITRONELLYL ACETATE.— This ester. C 10 H 1 yO.OC.CH 3 , 
is a natural constituent of geranium and rose oils, and is a useful 
addition to most rose or geranium perfumes. Its odour recalls 
that of bergamot oil. It is prepared by the acet 3 dation of 
citronellol, and has the following characters : specific gravity, 

0- 893 to 0-900 ; optical rotation, + 3° to — 3° ; refractive index, 

1- 4450 to 1-4480 ; and boiling point, 120° at 15 mm. 

C 3 H 7 , is prepared b}’' the suitable esterification of the alcohol. 
It is a useful ester to add in traces to artificial rose perfumes. Its 
specific gravity is 0-894, and refractive index 1-4465. 

GITRONELLYL FORMATE.— By acting on citroiieUol with 
concentrated formic acid, citroneltyl formate CiyHiyO.O.CH 
results. Commercial samples rarcty contain more than 90 per 
cent, of actual ester, as the reaction is incomjDlete. It is an oO of 
sijecific gravity about 0-910, and refractive index 1-4510. It has 
a faint rose odour with a suggestion of cucumber. 

GITRONELLYL TIGLATE.— See “ Tiglic Acid Esters.” 

GITRONELLYL VALERIANATE.— This ester has a fruity 
odour. Its specific gravity is 0‘888 ; and refractive index 1'4435. 

GIVET. — Of all the animal siabstances used in perfumery, 
civet probabl}^ has the most revolting odour, closely resembling 
fffices in this respect. In ver 3 ’' dilute solution, however, this 
odour is not noticeable, and it is an extremely valuable fixative, 
much appreciated for fine perfume work. It is a glandular secre- 
tion of the civet cat. The foUovdng account of the natural 
histoiy of this animal is due mainl 3 ’' to C. C. Treatt (P. cD E. 0. R., 
1912, 73. The civet cat tribe, the F? vendee, are confined to the old 
world. In this tribe are included other closely allied carnivors 
which do not produce civet, such as the mongoose and the 
ichneumons. All the true civet cats possess two perineal glands, 
forming a deep pouch in the posterior part of the abdomen, and 
this pouch is divided into two sacs, each about the size of a marble, 
in which the civet, secreted by the surrounding glandular foUicles, 



is stored. The civet iii the pouches is at first semi-fluid, but 
becomes stiffer, and darkens in colour. The function of the civet 
bag is not kuo^vn, but it is believed to be of value as a means of 
defence on account of its foul odour, and also for the purpose of 
sexual attraction. In spite of the foul odour, hounds will leave 
any other scent if they once cross the trail of a civet cat. The 
animals producing civet are the following ; Viverra zibetta, the 
Indian civet of Bengal, China and Malaya ; F. civeUina, on the 
Malabar coast ; F. incgaspila, the Burmese civet of Bimma, 
Cocliin China, the Malay Peninsula and Sumatra ; F. iangalunga, 
the Java civet of Java, Sumatra and Borneo ; and F. vialaccensis, 
the rasse of India, Ceylon, Assam, Cliina, Java and Sumatra ; 
and F. civcfla, the African civet cat. Almost the whole of the 
world’s supply comes from the African civet cat. It is possible 
that- the civet produced in other districts is used locally by the 
natives. Although always wild, the animal will sometimes 
become fairly tame in captivity, and the uniter (E. J. P.) has 
freely handled a number of the cats, wliich showed no tendency 
to bite. When, however, the civet is being collected, the cat is 
cj^uite unsafe to handle. It is placed in a long cage in which it 
cannot turn round, and teased and irritated, as the secretion is 
much greater when the cat is angered. The civet is extracted 
from the pouch -with a spatula, when it is pale yellow and semi- 
liquid, but hardens and darkens on exposure to the air, becoming 
rather stifier than butter. It is packed in ox horns, and protected 
by a leather cap tied roimd the horn, and exported in these horns, 
wliich usually hold about 30 oz. The bulk of it comes from 

Civet is very frequently adulterated, the principal adulterants 
being gummy and saccharine matter, banana pulp, or petroleum 
jelly. Civet owes its odour to a mixture of skatol, possibly indol, 
and a ketone termed zibethone, udth some free acids, ethylamine 
and propylamine (Sack, Chem. Zeit., 1915, 39, 538). Zibethone 
has the formula Ci 7 H 3 oO, and melts at 32-5°, boiling at 342° at 

A pure civet should have the following characters : — 

Water . 
klineral matter 
Acetone exti’act 
Dirt, hairs, etc. 

Petroleum ether extract 

Alcohol extract (90 per cent.) 

■ 167 

6-10 per cent. 

Not exceeding 2 p^ cent. 
Not less than 80 per cent. 
Not more than 5 per cent. 

Not more than 6 per cent. 
65-60 per cent. 


The acetone extract should have an acid value of from 85 to 
115, and the melting point should he from 42° to 4G°. 

The alcohol extract should have an acid value of about 135, 
and an ester value about 30. 

The following characters for pm-e civet are given by Schimmel 
& Co. {EericJU, 1924, lOG). 

Acid value. 

Ester value. 

i ' — 

Alcohol extract .... 
Ether extract (after alcohol) . 
Chloroform extract (after ether) 

Water ..... 

For cent. 











Adulteration with petroleum jelly causes a lowering of the 
alcohol extract, and an increase in the ether extract, the latter, of 
course, having a low ester value in the presence of petroleum jelly. 

The following method will detect petroleum jelly in civet. 
Five grams are well rubbed in a mortar with 50 c.c. of acetone, 
until it is completely disintegrated. The mixture is allowed to 
settle, and the clear liquid is poured off. The residue is well mixed 
with another 50 c.c. of acetone and then poured on to a filter, and 
the insoluble matter washed vdth a little more acetone. The 
residue is now dried at a low temperature. If the civet be free 
from petroleum jelly, it will be greyish-white in colour and 
powdery, whereas if the adulterant be present, it will be oily or 
pasty. In this case, the residue is well mixed vith 50 c.c. of 
petroleum ether, the liquid filtered, and the insoluble matter 
washed with more petroleum ether. In the presence of petroleum 
jelly the filtrate will almost always be fluorescent (uifless the 
petroleum jellj’’ has been completel}^ de-bloomed), and the solvent 
can be evaporated and the adulterant weighed. A nucroscopic 
examination should demonstrate the absence of vegetable cells 
and fibres, wliich are present if vegetable pulps have been used as 

Ai’tificial civet is a market article, but if^ entirely artificial 
lacks much of the value of true natural civet. A mixtmre of 
natural civet, however, "vvith synthetics, is more successful, and 
the best “ artificial civet ” is so compounded. Skatol, indol, and 
tetrahydro-pam-methyl-quinoline are the most useful sjmthetics 
for the purpose. 



Niviere has published an account of his examination of civet 
{Bull. Soc. Chim. (4), 1920, 27, 794), which is very illuminating 
in indicating the results to be expected with adulterated civets. 
Niviere examined four samples of civet described as pure. 

Sample No. 1 
„ No. 2 
„ No. 3 
„ No. 4 

Insoluble in Benzene 

Per cent, 

, 18-35 


in same. 




18*15 per cent. 

The ash in sample No. 4 was talc. 

After distillation of the benzene from the benzene extract in 

a vacuum, the soluble residues were dissolved in 96 per cent, 
alcohol. The amounts soluble in alcohol were as follows : — 

Sample No. 1 

„ No. 2 

„ No. 3 

,, No. 4 

Per cent. 






Calculated on the 
original weight 
of the civet. 

The acid numbers of the residues left after evaporation of the 
alcohol in vacuo varied httle; from 103*1 (No. 1) to 111 (No. 4) ; 
and the ester numbers varied from 15*3 (No. 1) to 25*2 (No. 4). 

The author continued the examination only on sample No. 2, 
as this presented the greatest probability of being pure. 

The benzene insoluble part melted at 58° to 59°, and in it 
cholesterine was identified mth certainty, and the following 
results were obtained : — 

Acid number 
Ester number . 
Iodine number . 
Acetyl number . 





_ These figures bear great resemblance to those furnished by 

Examination of the Alcoholic Extract. — ^The solvent was removed 
in vaciw and the residue taken up with ten times its weight of 
benzene. The solution at first was clear and limpid, but after a 
few minutes it became turbid, and a deposit appeared. The 
insoluble part was examined after, decantation. It was made up 
of glucose, which was identified by its physical properties and its 

The acids present in the benzene solution were removed by a 



5 per cent, solution of sodium carbonate, and constituted 0*35 per 
cent, of the crude civet. Tliej'' are liquid at the ordinary temiDera- 
tui’e, and then- odour suggests caproic and caprylic acids ; the 
average molecular weight was 168. 

After wasliing vdth water, the benzene solution was exhausted 
with 5 per cent, sulphmic acid, and yielded skatol and some 
volatile bases with an odour of ethylamine and propylamine. 

After removal of the solvent, the remaining fraction, 57-2 gram 
was fractionally distilled in vacuo, and yielded, at a pressme of 

5 mm : — 


(a) 145°-180° .... 3-00 

[b) 180°-200° .... 7-00 

(c) 200°-210° .... 6 00 

[d) 2]0°-220° . . . .20-80 

(c) 220°-230° .... 9-40 

(/) 230°-280° . . . .9 00 

Residue ..... 9'00 

Several of these fractions did not possess the characteristic 
odour of civet : the}’' had the odom' of a fatty body somewhat 
rancid. The fraction (cZ), which was solid, smelt Hlce rancid 
stearme ; its meltmg f»omt was not very sharp, about 70° ; its 
acid number, 198*4 ; and acetyl number, 160. It was, therefore, 
chiefly made up of an acid containing hydroxyl, similar to those 
present in -wool fat. Niviere concludes that this sample was 
adulterated with lanohne, and probably liquid glucose. 

CLARY SAGE. — Salvia Sclarea, Imovm as clary sage, or 
muscatel sage, jdelds an essential oil the value of wliich cannot 
be over-estimated for perfumery purposes. The plant is a native 
-of the Mediterranean littoral, and has long been used by the 
Itahans in the preparation of vermouth, and by the Germans 
in giving wine a “ muscatel ” flavom,’. Gattefosse is mainly 
responsible for having brought its great perfume value into due 
prominence, and in 1909 he started its cultivation on a com- 
mercial scale in the Vaucluse district. It flourishes best in the 
warmer districts, such as Vaucluse, Basses-Alpes, Var, Alpes 
Maritimes, Gard, Herault, and Ariege. It is commonly known 
as muscatel sage or toute bonne. It prefers a light, stony soil. 
It is usually cut tA’sdce a year, firstly in Juty, and, later, in 
September. The first cutting is the richer in essential oil, the 
second being usually dried as a herb instead of being distilled. 
Propagation is usually effected by means of seeds, the 3’-oung plant 



growing to a height of about 1 8 inches in the first year, and 4 to 6 feet 
in the second j^ear. The crude oil (or the substances extracted 
bj’- means of a volatile solvent) has such a high fixative value, 
combined with a useful odour, that it has become known in 
Trance as huih amhrte, oil of amber, or vegetable ambergris. It 
is an expensive oil, as the yield is quite small. In distilling the 
oil lavender stills ma}'- be used, but rapid distillation with high- 
pressure steam and higlil}’’ efficient condensation are essential. 
When the plant is conveyed by road to the distillery, there is 
usually a considerable time between the gathering of the plant 
and its distillation, so that a certain amount of fermentation 
takes place, and the product is less valuable than when distillation 
follows the cutting immediately. If the wdiole of the plant be 
distilled, including the roots, the oil may contain resinous and 



gravity at 20®. 





Per cent. 


- 11° 

Vaucluse . 



— 16-6° 




— 22-1° 



— 23-6° 





— 14-6 









JJ • • 




oxygenated bodies of powerful odour. Tliis type of oil is useful 
enough for fixative purposes, but is not of the delicate odour 
necessary for the finest perfumery purposes. Where such an 
oil is required, only the flowering tops should be distilled, W’-hich 
are encouraged by liberal manuring. The character of the ofi. 
varies with the state of matmity of the plant, the degree to which 
the plant has been dried, and the time and weather when the 
plant is cut. Tor example, a pure oil may contain as little as 
38 per cent., or as much as 72 per cent, of esters, calculated in the 
conventional manner as linalyl acetate. Tine oils, distilled only 
from the inflorescences, are freed from resinous matter, wliich 
is separated in the distillation and dissolved in inferior grades 
of oil to be used solely for fixative purposes. The fine grades of 
oil have an exquisite odour recalling neroli, bergamot, lavender-, 
and ambergris. It can be used in nearly any type of fine perfume, 





1G0.J, when they were expelled bj* the Dutch. On the founding of 
Penang by Captain Light in 1786 the East India Company tried 
to break the Dutch monopoly, and the cultivation proceeded 
slowly, but steadily, and Penang cloves are still amongst the 
most highly esteemed, but the greater part of these are consumed 
locally, so that a great deal does not reach the London market. 

The word clove is derived from the French clou, a nail, from 
the resemblance in shape of the dried bud to a nail. 

The plant is generally grown from seed, but can also be propa- 
gated by means of la3'crs. Seeds are soaked in water for several 
da3’s, and when the3' have commenced to germinate the3’- are 
planted out about G inches apart in shaded beds, with the bud 
end above the ground. The plants are kept in these beds, well 
.shaded and watered for nearly a 3*ear. When the3’’ are about 
6 inches tall the shading is removed, and the3’’ are hardened off 
by exposure to the sun for a month or two, and then planted out. 
The most suitable soil is a dark loam with a substratum of dark 
3^ellow earth mixed vuth gravel. In Zanzibar a red clay soil is 
preferred. The tree onl3’’ grows successfully fairl3’’ near the coast, 
and is said to require sea air. The clove tree commences to pro- 
duce flower buds in the fourth or fifth 3'ear after planting, in 
Penang and Zanzibar. In the Moluccas, this takes six to eight 
years. The buds are read3’' for gathering in August to December, 
in Zanzibar, and about a month later in the Straits Settlements. 
In the ]\Ioluccas the harvest takes place twice a 3'ear, namely, m 
Jul3’- and December. The buds are generall3^ l)icked off b3’' hand, 
and are then spread out on mats to dry in the sun. In Ambo3ma 
the3' are first dried on a framework over a slow wood fire, which 
gives them a brown colour, and then are dried off in the sun, 
when the colour changes to black. In Zanzibar, after the clove 
buds are gathered, they are dried for six or seven da3’^s, during 
wliich time they lose up to 60 per cent, of their weight. Zanzibar 
cloves are smaller and more shrivelled, and of poorer colour, than 
Penang and Ambo3ma cloves. The best cloves are large and 
plump, but little wiinkled, and of a light purplish brown vdth a 
purplish bloom on them. If gathered before they are ripe, the3'- 
shrinlc and become shrivelled badly, whilst if insufficiently dried 
they are liable to go mould3’’. For exhaustive details of the 
cultivation and histor3’' of the spice, H. N. Ridley’s work “ Spices ” 
(Macmillan, London, 1912), should be consulted. The flower 
stallfs,- separated from the buds whilst they are df3dng, are also 
dried and exported, and are distilled for their essential ofi, which is 




present to the extent of about 6 to 7 per cent., as against 12 to 
18 per cent, in the buds. These stems are known in France as 
grijfes de girqfle. The dried fruits of the clove are known as 
mother cloves ; these are occasionally exported, but are not. 
usual articles of commerce. 

Cloves are distilled to a very large extent, probably far in 
excess of any other sj)ice. The oil is obtained to the extent of 
12 to 18 per cent., sometimes even up to 21 per cent. It is used to 
a certain extent in medicine, to a considerable extent as a flavour- 
ing material, and on a verj^ large scale as a raw material in the 
perfumery trade. A genuine clove oil has a specific gravity 
1*044 to 1*070 ; optical rotation, — 0° 20' to — 2° 30' ; and 
refractive index, 1*5290 to 1*5355. It contains from 78 to 98 per 
cent, of eugenol. 

Eugenol is the prmcipal constituent of the oil, and upon its 
percentage the oil is valued. There are present also a small 
amount of acet-eugenol, the sesquiterpene caryophyllene, traces 
of eugenol ethers, vanillin, salicylic acid, methyl benzoate, am 3 d- 
methj'l ketone, heptyl-methyl ketone, methjd-amjd carbinol, 
methjd-heptjd carbinol, benz 5 d alcohol, and dimethjd furfurol. 

The eugenol is extracted from clove oil b}^ absorption with a 
solution of caustic alkali, from which it is set free on acidification. 
A small quantity of eugenol is used as such in perfumer}^, in the 
manufacture of clove and carnation odours, and a certain amount 
is converted by heating with alkali, into its isomer isoeugenol, 
which has a finer carnation odour, and is used for the same per- 
fumes. The built of the eugenol so obtained, however, is used for 
the manufacture of vanillin {q.v.), wdiich is used on an enormous 
scale for chocolate flavouring, and to some extent also in per- 
fumery. Eugenol is invariably determined in the oil, in practice,’ 
by means of an absorption with caustic alkali solution {vide 
“ Phenols, Determination of ”), but the process devised by Thoms 
is probably a little more accurate. (See E. J. Parry, “ The 
Chemistry of Essential Oils,” 4th ed., vol. i., j). 333.) 

The oil distilled from clove stems does not differ material^ 
from that of clove buds. A sample of the oil distilled from 
mother cloves was found by Schimmel & Co., to have the following 
characters: specific gravity, 1*053; optical rotation, — 3°11' ; 
refractive index, 1*5433 ; and eugenol value, 88 per cent. Clove 
leaves yield from 4 to 6 per cent, of an oil having a specific gravity 
1*032 to 1*067 ; optical rotation, — 0° 30' to — 2° ; refractive 
index, 1*5320 to 1*5390 ; and eugenol content, 75 to 93 per cent. 


P B n F U 21 E B Y 

The residue of clove oil fx'om the eugenol manufacture is used 
as a cheap soap perfume imder the name “ light clove oil.” 

COGNAC OIL. — Oil of cognac is used for flavouring, and, 
to a small extent, in perfumer^-. The natural oil is obtained 
during the ixrocess of fermentation of the grajxe juice bj’- the 
j'east, and is prepared by distilling the residues of the vine used 
for the production of brandy, or from the yeast cakes remauiing 
after the removal of the vine. The development of the aroma of 
Avine has been elaboratelj’’ investigated bj'^ Rosenstiehl {Compies 
Bendus, 190S, 146, 1224, 1417 ; 1908, 147, 150). He found that 
the partieular esters developed depended, not only on the character 
of the grapes employed, but also on the miero-organisms that 
develop on the fruit. The crude oil is usually of a greenish colour, 
on account of traces of copper in combination vith free fatty 
acids. If the copper be removed by shaking vith tartaric acid, 
and the free fatty acids b}’- shaking AAith dilute caustic soda 
solution, a purer oil is obtained. The physical characters of the 
oil are very variable, and to a great extent depend on the degree 
of rectification to which the oil has been subjected. The folloAving 
values cover most genuine sainples : — 

Specific gravit 3 '’ . 
Refractive index 
Optical rotation . 
Acid value 
Ester value 

0- 870-0-890 

1- 4270-1-4325 

— 0° 30' to + 0° 45' 

For the occurrence of traces of meth 5 d anthranilate in cognac 
oil, see PoAver and Klleber, Jour. Agric. Besearch, 1923, 23, 47. 

It was first considered (Pelouze and Leibig, Annalen, 1836, 19, 
241) that the chief constituent of oil of cognac Avas the ethyl ester 
of oenanthjdic acid, and that the latter was identical vith pelar- 
gonic acid obtained from rose-geranium oil. Later investigations, 
hov'ever, showed that oil of cognac is a mixtine of esters of ethji 
and amyl alcohols and capric and caprylic acids (Eischer, Annalen, 
1861, 118, 307 ; Grimm, ibid., 1871, 157, 264 ; Halenlxe and 
Kurtz, ibid., 1871, 157, 270). 

The term “ oenanthic ether ” is usually applied to the natural 
product, but artificial esters are prepared which have an odour 
resembling the true oil of cognac^ These are the ethyl esters of 
cenanthylic and pelargonic acids. 

OEnanthylic acid CH 3 (CH 2 ) 6 COOH is normal heptoic acid, and 
is obtained by the oxidation of cenanthol, produced by the 


PERFU 21 E R r 

destructive distillation of castor oil. It is also formed by the 
oxidation of normal lieptyl alcohol and of oleic acid, and by the 
reduction of dextrose-carboxyhc acid. It is an oily liquid boiling 
at 220° to 223°, and has a specific gravity of 0*918 at 20°. 

QSnanthal, oenanthic aldehyde or normal heptylic aldehj'-de is 
obtained by the dry distillation of alkaline ricinoleate. Castor 
oil, wliich consists essentially of the glycerides of ricinoleic acid, 
is rapidly distilled until a resinous residue remains, the greater 
part of the ricinoleic acid being converted into cenanthal and 
higher fatty acids. The distillate is rectified and the portion 
distilling between 90° and 180° shaken with- a saturated solution 
of sodium bisulphite, warmed, and filtered. The salt, which 
separates on cooling, is pressed between filter paper, mixed with 
sodium carbonate, and distilled in a current of steam. The 
cenanthal wliich floats on the distillate is separated and dried over 
anhydrous sodium sulphate. A better yield is obtained by 
distilling the ethyl or methyl ester of ricinoleic acid. 

Ethyl pelargonate is prepared by the action of dilute nitric acid 
on oil oT rue. The oil is treated vfith tvdce its weight of dilute 
nitric acid and heated until the mixture begins to boil. Two 
layers are formed, the upper one containuig the cliief produets 
of oxidation. The lower layer is freed from nitric acid by heating 
on a bath containing a solution of zinc chloride. The two liquids 
are then filtered, and the pelargonic acid is converted into the 
ethyl ester by esterification with alcohol, and purified by steam 

CONCRETES. — See “ Extraction of Perfume from Plants.” 

CONV ALLARIA MAJALIS. — ^This is the lily of the valley. 
The perfume is prepared in the form of a concrete or absolute, 
but as found in the market is mainly synthetic. (See Lily ” 
and “ Muguet.”) 


CONVOLVULUS OIL. — ^The wood of Convolvulus scopavius 
and G. floridus, both indigenous to the Canary Islands, yields a 
small quantity of essential oil, which is the true rosewood oil, or 
oil of rhodium. It is a liquid which sohdifies at low temperatures, 
melting again at 11° to 12°. Its general characters are not known 
with certainty, as the authenticity of most samples examined is 
doubtful. The oil as met with in commerce is almost entirely 
an artificial mixtiu’e. It is used in soap perfumery, and must not 
be confused with the oil of Bois de Rose. 


PEBF U JI E li r 

CORIANDER, OIL OF.— This oil, occasionally used in per- 
fumery, for example in traces in eau de Cologne, is distilled from 
the rijje fruits of Coriandrum sativum, a native of the Levant and 
southern Europe. The oil contains dca-h’o-linalol, pinene, and 
other constituents not j^et identified. It has a specific gravity 
0-S70 to 0-885 ; optical rotation, -f- 7° to -f- 14° ; and refractive 
index, 1-4035 to 1-4760. (For the liistory, etc., of tliis spice, see 
Eidlej", “ Spices,” p. 384.) Indian distillates sometimes have a 
refractive index as low as 1-4569. 

CORIANDROL. — ^An old name for impure linalol when 
extracted from coriander oil. 

GORYLOPSIS. — ^The Japanese plant Corylopsis spicala 
bears highly odorous flowers which have a heavy, somewhat 
sickly odour, Iflce that of many orchids or lilies. The perfume is 
not extracted, but the name is applied to fancy perfumes wliich 
have some slight resemblance to the natural odour. These are 
usually based on infusions of rose, jasmine, tuberose and orange 
flowers, with the addition of a little vetivert or patchouli oil, 
hydroxy-citronellal, terpineol, ylang-jdang oil, and a trace of 
artificial essence of strawberry. 

GOUMARIN. — Coumarin is one of tlie most important of the 
artificiaUj'- prepared perfumes. It is the substance to which the 
Tonquin bean (Tonlca bean) owes its odour ; it is found in 
appreciable quantity in the leaves of the American “ deer’s 
tongue,” Lialris odoraiissima, and has been found in a large 
number of other plants in smaller quantity {vide E. J. Parry, 
“ The Chemistry of Essential Oils,” 4th ed., vol. ii., p. 272). 
Commercial coumarin is invariably the artificial product. It was 
first prepared synthetically by W. H. Perkin {Chem. Soc. Jour., 
xxi., 53, 181) by heating salicylic aldehyde (q.v.) with acetic 
anliydride and sodium acetate. Tiemann and Herzfeld heat 

3 parts of salicylic aldehyde, 5 parts of acetic anhydride, and 

4 parts of fused sodium acetate on an oil bath for twenty-four 
lionrs. Water is then added, and the oil which is precipitated is 
separated. This consists of acetyl-or/7io-coumaric acid, with a 
little coumarin. This acid is decomposed by heating it to a little 
below its melting point (146°) into acetic acid and coumarin. 
RascHg first prepares oriZjo-cresol carbonate by the action of 
phosgene on or^^o-cresol in the presence of pyridine. A current 
of chlorine is passed through this ether at 180°' which results in 
the formation of di-chlor-o-cresol carbonate. On hydrolysis this 


PE B F U 31 E B Y 

yields salicjdic aldeh 3 ’^de, from which coumarin is prepared as 
above described. Hugo Weil has patented a method depending 
on the reduction of salicyhc acid by sodium amalgam in the 
presence of boric acid. The sahcyhc aldehyde is, as it is formed, 
combined with paratoluidine. For example, 15 parts of salicyhc 
acid, 5-5 parts of sodium carbonate, 1,000 parts of water, 18 parts 
of toluichne, 250 parts of salt, and 15 parts of boric acid are mixed 
and treated with 325 to 425 grams of a 2 per cent, sodium amalgam. 
The liquid is kept acid by the addition of boric acid. The ortho- 
oxj^-benzylidene-paratoluidine is filtered off and dissolved in a 
faintly acid solution which, on steam distillation, jdelds sahcyhc 
aldehj'^de, which is converted into coumarin in the usual 

Coumarin is a highly odorous substance melting at 68 °, and 
havmg the characteristic odour of Tonquin beans. It is a basic 
material for aU perfumes of the t 5 qoe of foin-coupe, or “ new-mown 

It is often adulterated with acetamhde and with terpin hj’^di’ate. 
The former is detected bj^ heating the sample with a solution of 
caustic potash and adding a few drops of chloroform, when, on 
boilnig, the intense odour of phenjd isoc^’^anide is evolved. Terpin 
liydrate is recognised bj^^ boiling the crystals with dilute sulphuric 
acid, when the odour of terpineol is at once noticed. 

CRATEGINE. — This body is identical vdth anisic aldehyde, 
either pure or in a reduced condition. 

CRATEGUS OXYCANTHA. — See “ Hawthorn.” 

CREOSOL.— This body is a diphenol, C 7 H 6 (OH) 2 , occurring 
in oil of ylang-ylung. It is an odorous oil, boiling at 220°. 

CRESOL (META-). — This body is a cr 3 ’’staUme substance of 
the formula C-HgO, melting at 4°, and boihng at 201 °. It ocem’s 
to a small extent in essential oil of myrrh. It is used in the 
manufacture of artificial musks. It is a colourless liquid of 
specific gravity 1-0375, cr 3 ^stallising at 10° to 12°, and boiling at 
202° to 203°. 

CRESOL (PARA-) . — ^This bod 3 ’-, isomeric vdth ?7ieto-cresol 
C^HgO, is a crystalline body melting at 36°, and boiling at 199°. 
It is found in the oils of jasmin and cassie flowers. 

CRESOL (PARA-) BUTYL ETHER.— This ether, C 7 H 7 . 
O.C 4 Hg, is prepared by the condensation of pam-cresol and but 3 d 


PE BFU 31 E P y 

alcoliol by means of lij’drocliloric acid. It is useful in the prepara- 
tion of artificial ylang-ylang and similar odours. 

CRESOL (PARA-) METHYL ETHER.— This body, of 
the formula CyH^.O.CHg.-is a natural constituent of ylang-ylang 
and other flou'er oils. It is a colourless liquid, darkening on 
keeping, with a powerful odour, which recalls that of wallflower, 
on dilution. It boils at 175°, and 3 delds anisic aldehj'de on 
oxidation. It is essential for the production of artificial flower 
oils of the jflang-jdang and wallflower t 3 ’’pes. It is prepared 
artificiall 3 ^ b 3 '’ condensing poru-cresol with methyl alcohol by 
means of h 3 'drochloric acid. Its specific gravit 3 ’ is 0-f)75 to 0-977, 
and refractive index 1-5130. 

isomeric vith the corresponding para-cres 3 d derivative. It has a 
sweet, heav 3 ’- odour, and is useful in the preparation of 3 dang-ylang 
and other exotic floral perfumes. 

CRESYL OXIDE. — There are three cresyl oxides, correspond- 
ing with the three isomeric cresols. The 3 '^ have the formula (C 7 H 7 ) 20 . 
The best knovm is the di-o? 77 io-cres 3 d oxide, which boils at 275°. 
It is prepared b 3 ’’ dehydrating cresol, or by distilling cres 3 date of 
aluminium, or by condensing bromotoluene with cres 3 date of 
potassium in the presence of finely powdered copper. It is useful 
as a variant of phen 3 d oxide in the preparation of artificial 
geranium perfumes. 

CRESYL (PARA-) ACETATE. — This acid ester of cresol 
CH3.COO.C7H7 is prepared by the interaction of ^ora-cresol and 
acetic anh 3 ’'dride, or of the sodium compound of the phenol and 
acet 3 d chloride. It has been known as narceol. It has a powerful 
narcissus odour. It has a specific gravit 3 '’ 1-0528, and refractive 
index 1-5040. 

of , a sweeter narcissus odour than the corresponding acetate. It 
has the constitution CeH 5 .CH 2 COO.C 7 H 7 . 


usual times at which the more important of the French flowers 

are gathered for treatment are as follows : — 


February-IIarcJi : . Cassie, violet, mimosa, hyacinth. 

Ax>yil .... Jonquil, h 3 ^acirith, narcissus, violet, 



P Eli F TJ 21 E R Y 

Hay . 

June . 

J uly . 

October— N overnber 

Jonquil, narcissus, orange flowers, rose, 
rosemary, thyme, broom, carnation. 
Kose,_petitgrain, mignonette, carnation. 
Jasmin, lavender, rose, rosemary 
thyme, tuberose. ’ 

Tuberose, lavender, jasmin. . ' 

Cassie, jasmin. 

GULILAVAN OIL.— Culilavan oil is distilled from the bark 
oi Cmnamomum Culiaivan. It is an oil of specific gravity l-OSO 
o -055, ai;d contains about 60 per cent, of eugenol, with a small 
quantity of methyl eugenol and terpineol. 

hvde^^H This body (p-isopropyl benzaldo- 

njae UigJliaU) is a natural constituent of cassie flower oil, but is 

foimd to a much larger extent in cummin oil. It has a powerful 
odour, and should only be used in traces in floral perfumes It 
has a specific gravity 0-982, and boils at 236° 

CUNNINGHAMIA SINENSIS —This tree, ' growing in 
lonkm, yields a^ wood which is known as “ coffin wood,’’ or 
^ san-mou. ’ This is used to make coffins which are said to be 
mdestructible, joss sticks, and other preparations for burnino- 
Gardies (La Parfumerie Moderne, 1923, 110) has examined the 
essential oil, which has an odour of terpineol and cedrol, and found 
it to have the following characters : specific gravity, 0-957 • 
optical rotation, — 23° 6' ; refractive index, 1-4932 ; esters' 
7-4 per cent. ; and free alcohols, 29-4 per cent. 

CUS-CUS. — See " Vetivert Oil.” 

CYCLAMEN.— There is no natural perfume extracted from 
the cyclamen as a commercial article. Various species of perfume- 
bearing plants are found growing wdld in the Alpine regions, of 
which Cyclamen persicum is one of the sweetest scented The 
odour of the flowers is of the amaryUis or lily type, and is 
matched, to some extent — but only as a fancy perfume which 
does not, in fact, reproduce the odom’ of the flower — ^by the use 
of hydrox3’^citronellal, ionone and phenyl-acetic aldehyde, vdth 
traces of terpineol, and some weak floral basic perfume such as 

cinnamic alcohol. A trace of acetic ether gives tone to this 

does not^ occur naturally. It is prepared by the action of 
phosphoric acid on geranyl acetate at a low temperatiire, and by 



then dehydrating the glycol so formed by means of phosphoric 
acid at 40°. It is an ester with a sweet odom' of fresh flowers. 

CYMBOPOGON OILS. — See under Citronella, Lemongrass, 
Palmarosa, and Gingergrass Oils. Also “ Cymbopogon Nervatus, 
Oil ofj” etc., and under Grasses (Perfumed) of India and Cejdon.” 

CYMBOPOGON GAJSIUS.— This grass is closel}' allied to 
C. Martini, but is distinctly different. Where the two grasses 
meet, transition foi'ms occur in which the two species unite 
completely*. Pew details as to the oil ai’e available. (See Adminis- 
irafive Rej}ort of the Government Botanic Gardens and Parks in the 
Nilghirisfor 1901, ji. 5. See “ Iniclii Grass.”) 

CYMBOPOGON COLORATUS. — Samples of the oil dis- 
tilled from this grass in the Fiji Islands examined at the Imperial 
Institute (Bull. Imp. Inst., 1912, 10, 27) were found to have the 
following characters : specific gravity, 0-911 to 0-920, and optical 
rotation, — 7° to — 11°. One sample contained 40 per cent, of 
aldehydes, principally citral, 23 per cent, of geraniol, and 10 per 
cent, of esters, piincipally geranyd acetate. A second sample 
contained 15-6 per cent, of geraniol, and from 45 to 50 per cent, 
of citronellal. 

CYMBOPOGON JAVANENSIS.— This grass yields a 
highly aromatic essential oil with a sweet odour, resembling 
palmarosa oil. It has been examined by Hofman (Pharm. 
Werkhlad, September 6th, '1919). It had a specific gravity 0-975 ; 
optical rotation, — 3° ; refractive index, 1-5135 ; acid number, 
1-25 ; geraniol content, 4S per cent. ; esters, 14-3 per cent. ; and 
methyl-eugenol, 30 per cent. Citral, Zeero-pinene and methyl- 
isoeugenol are also present in the oil. 

CYMBOPOGON NERVATUS.— This plant is the Naal 
grass, found very widely distributed in the central portions of the 
Sudan, being abundant in the Blue Nile, Fung, and Kordofan 
provinces. The grass, when collected in full fiower, in the autumn, 
yields the highest amount of oil— varying from 0-8 to 1-5 per 
cent, of the weight of the dried grass. The infiorescence alone 
is of value for distillation, as the stalks contain very little' oil. 
The oil was reported upon by ScJdmmel cO Co. (Report, April, 
1911, 19), but from details published by Joseph and Whitfield 
(P.' c& E. 0. R., 1922, 175), it is probable that the oil they examined 
was not a genuine one. The oil obtained by these chemists was 
pale yellow in colour, and in odour closely resembles gingergrass 

' 171 

P B P F U M B R Y 

oil — the so-called “ Sofia oil " distilled in India from Gymhopogon 
Martmi. Three samples had the following characters : 





Specific gravity at ^ . . . j 




Refractive index 




Optical rotation .... 

— 31° j 

I — 35° 

— 50° 

Acid value ..... 




Ester value ..... 




Ester value, after acetylation . 




Naal oil contains Zcez/'O-limonene and porillic alcohol. 

CYMBOPOGON POLYNEUROS.— This grass, growing 
freely in Ceylon, ^fields an odorons essential oil having the 
following characters : specific gravit}’", 0*936 to 0*951 ; optical 
rotation, -f 31° to -{- 53°, and containing 38 to 52 per cent, of 
aromatic alcohols. 

GYPERUS ROTUNDUS, OIL OF.— Joseph and Whit- 
field {videP. cb B. 0. i?., 1922, 176) have described this oil, which 
is known as Seid oil. The plant grows in the Nuba Mountains 
province, about twenty nules to the east of the White Nile, and 
about 350 miles south of Kliartoum. The plant, which is a sedge, 
gTows freely in the Sudan, and the rliizomes yield 0*5 per cent. 


an aromatic essential oil, of specific gravity at 

20 ° 

2 ^’ 

0-955 ; 

optical rotation, — 20° ; and iv3fractive index, 1*4967 at 25°. 

caUed mahareb grass of the British Sudan yields about 1 per 
cent, of a fragrant essential oil, wliich somewhat recalls penny- 
royal. Roberts {Jour. Gli&rn. Soc., 1915, 1465) states that it has a 
specific gravity 0*938 to 0*942 ; optical rotation, -f 29° to -f 34° ; 
and ester value after acet 3 dation, 60 to 62. The oil contains 
pinene and limonene, menthenone, a sesquiterpene alcohol, an 
alcohol of rose-hlce odom-, higher fatty acids in the form of esters; 
traces of a phenol, and one or more sesquiterpenes. 

CYMYLACETIG ALDEHYDE.— This body (l-isopropyl-4- 
ethanal-benzene), of the formula (CH 3 ) 2 .CH.C 6 H 4 .CH 2 .CHO, is 
obtained by the condensation of magnesium cymyl chloride with 



ethyl orthofoimate, hydrolysing the product -ndth dilute sul- 
phuric acid, and separating the aldehyde by means of its bisulphite 
compoimd. It is a pale yeUow liquid, boiling at 243°. It has a 
strong verbena bdoitr, and may find emploj’^ment in sjoithetic 
perfumery (Best, Comptes Eendns, 1923, 550). 

Dacrydnim Franklinii, which grows only in Tasmania, where it 
is known as the Huon pine, jdeld 0-5 per cent, of essential oil 
having the following characters : — 

Specific gravity .... 0-8677 

Optical rotation , . . .4-20*5° 

Refractive index . . ' . . . 1-4835 

It consists mainly of terpenes, but there is also present a small 
amount of methyl-eugenol. 

The wood yields about 0-5 per cent, of oil having the following 
characters : — 

Specific gravity at 18° 
Optical rotation 
•Refractive index at 23° 
Acid value 
Ester value 

4- 0-6° to 4- 1-4° 
0-9-3- 1 

■ This oil consists almost entirely of methyl-eugenol. It has 
recently been examined at the Imperial Institute {Btdkiin, 
vol. xxii., No. 3, 1924) and the following results recorded : — 

Specific gra-vdty at 1.5/15° C. 


Optical rotation aD . 

. - 3-75° 

Refractive index nD . 


Acid value 


Ester value before acetylation 


Ester value after acetylation 

. 11-2 

Solubility in 70 per cent, alcohol 

. Soluble in 

1-5 vols. 

On distillation, about 90 per cent, of the 

oil passed over between 

250° and 253° -under 755 mm. pressure, and consisted essentially 
of methyl-eugenol. The results of the investigation show that 
the composition of the present sample of Huon pine oil agreed 
with that recorded for the oil by previous observers. Methyl- 
eugenol is used to some extent in perfumer}’-, ■ but no regular 
demand has hitherto arisen for Huon pine oil, although it is clear 
from the results of the inquiries made by the Imperial Institute 
that there is likely to be a demand for it if it can be supplied in 
commercial quantities and at a reasonable price. 



DAFFODIL PERFUMES. — These are inerety rariations of 
narcissus odours, or, in fact, often identical except in name. 
{Vide “ Narcissus.”) 

Boorsma [Bull, du Dip. d' Agricult, aux hides Neerl., 1907, 7, 25), 
the wood of Dalbergia Cuiniiigiana, which is found in Dutch 
East Indies, yields about 0-5 per cent, of an essential oil of 
aromatic odour having the following characters : — 

Specific gi’avity at 26° . . . 0-891 

Optical rotation . . , , — 4° 31' 

Ester value ..... 5 

Ester value after acetylation . . 116 

The wood is known localty as Tcagii laha. 

DARWINIA OILS. — The essential oils of several species of 
Danvinia, growing' in Australia, have been found to have distinct 
perfume value. They have been investigated by Baker and 
Smith {Jour, ds Proc. Boyal Society Neiv South Wales, 1899, 163 
and 1916, 181). The oil distilled from Darwinia fascicularis, a 
shrub found in the neighbourhood of Port Jackson, was obtained 
to the extent of 0-45 per cent. It has a specific gravity 0-916, 
is slightly dextrorotatorj’-, and contains from 55 to 63 per cent, of 
geraniol, mostly in the form of geranyl acetate. The oil from 
Darwinia iaxifolia has a specific gravity 0-876, and an optical 
rotation — 6-6°. It contains a small amount of an alcohol, which 
is probably linalol. The oil from Darwinia grandiflora (originally 
knoAvn as D. iaxifolia, var. grandiflora) has been examined by 
Baker and Smith, and more recently by Penfold [Jour, and Proc. 
Boyal Soc. N.S.W., Ivii., 237). The oil has a specific gravity 
from 0-901 to 0-9165 ; and optical rotation, + 18-26° to -j- 27-65°. 
The oil contains dea;/?*o-pinene, a sesquiterpene alcohol, and esters 
of an alcohol which has, provisionally, been named darvdnol. 
This body has the formula CjoHigO, and possesses the foUovdng 
characters : — 

Boihng point at 10 mm. 108° to 111° 

Specific gravity . . O’ 955 9 

Optical rotation . . + 38’6° 

Refractive index . . 1-4918 

DAUCUS, OIL OF. — ^The seed of the common carrot 
{Daucua Caroia), yields an essential oil which has a distinct 
perfume value. The jdeld is from 1 to 1-5 per cent., and the oil 
has the following characters : specific gra’vdty, 0-870 to 0-946 ; 



optical rotation, — 11° to — 40° ; refractive index, 1'4S20 to 
1-4920 ; and ester value, 17 to 55. The oil contains terpenes, and 
a divalent sesquiterpene alcohol, C15H26O2, melting at 115° to 11G°, 
and which has been named daucol. Roure-Bertrand Fih {Bulletin, 
April, 1912, 30) have examined the oil distdled from the entire 
plant at the period of maturity of the seed, and found it to have a 
specific gravity 0-902 ; optical rotation, — 7° ; and saponifica- 
tion, 195. The essential oil of the closelj’’ sBiod DaucusGingidium 
has a rather finer odour* than the ordinary carrot oil. It is prac- 
tically identical in general characters with carrot oil, containing 
daucol as its odorous constituent. The oil has an odour recalline 
that of orris oH, and is of great value in toning dovui the some- 
what crude odour of pure ionone and similar synthetic violet oils. 

DECALEPIS HAMILTONII. — ^By the steam distillation of 
the crushed fresh roots of Decalejns Ilamiltonii, a plant used 
cliieflj’- as a condiment in hfysore, a bromnsh solid substance has 
been obtained which crj’-stallises in the condenser. Treated rvith 
a little animal charcoal and redistilled, it forms a pure white 
crystalline body melting sharply at 41°. It is probablj’- identical 
with the crystalline body isolated by Goulding and Pelly {Proc. 
Cliem. Soc., 1908, 62, 1911, 235) fi'om a species of chloroeodon 
roots. It has an aromatic odour similar to that of vanfilin. 

DEGINE CARBONATES.— See “ Heptine Carbonates.” 

DEGYL ALCOHOL.— This alcohol, CH3(CH2)8CH20H, is 
the most useful of the higher fatty alcohols {vide “ Alcohols, 
Higher Fatty ’'). It melts at — 10°, and boils at 231°. It is 
exceedingly useful for giving a new tone to fioral odours. Its 
specific gravity is 0-833. 

DEGYL ALDEHYDE. — See “ Aldehydes, Higher Fatty.” 

ment Oil.” 

DEODAR. — See under “ Cedarwood Oil.” 

DEPILATORIES. — These substances rank among the less 
dignified articles included in the perfumer’s art. Comparatively 
large quantities are exported to the East, and many women in the 
West elect to risk damage of a disfiguring nature to their skins 
for the sake of removing superfluous hairs. Alkaline sulphides are 
the basis of many of these preparations, calcium hydrosulphide, 
strontium hydrosulphide, sodium sulphide and barium sulpliide 
being those principally used, frequentty in admixture with 

175 • 


powdered quicklime, and diluted uitli starch, sugar or talc. 
These preparations convert the hairs into a gelatinous mass, but 
only attack normal skins after repeated employment, Rushma, 
a favoiu'ite preparation in the Eastern harems {vide Durvelle, 
“ Perfumes and Cosmetics,” p. 313) is essentially a preparation 
of arsenic sulphide (orpiment) and lime with a httle sulphur. 
Thallium acetate, in combination with zinc oxide, has been 
recommended as a depilatory ; it appears to be ver}’- powerful, 
but not to attack the roots of the hair, so tliat its effect is quite 

DEVARDARI OIL. — ^The wood of Erylliroxijlon mono- 
gynum, the so-called bastard sandalwood of India, yields about 
0-25 per cent, of an odorous essential oil having the following 
characters ; specific gravity, 0*983 ; ojJtical rotation, + 16° ; 
refractive index, 1*5140 ; and containing about 40 per cent, of 
a sesquiterpene alcohol. The oil has a sandalwood odour, and is 
of use in cheap perfumery where tliis odour is required. 

DHELUM WANGI. — ^This plant, also known as Tilam 
wangi or Dilem icangi, is the true patchouli, under cultivation, 
as a rule, for distillation pinqooses. DJiclv.m ouian is a wild 
patchouli, of unknomi botanical origin, which is sometimes added 
to the true leaves for distillation, {Vide “ Patchouli Oil.”) 

DIACETINE. — This is an artificial ester, or a constituent of 
commercial triacetine, which is used for adulterating ester-con- 
taining oils. It is a practical^ odourless body, having a specific 
gravit 3 '’ 1*184, and boiling point 260° to 265°. One part of this 
body indicates 2*22 parts of esters returned as linaljd acetate. 
{Vide “ Esters, Artificial.”) 

DIAGETYL.— This body is a diketone, CH3.CO.CO.CH3, found 
in the distillation waters of sandalwood, orris, savin, carawaj’’, and 
various other essential oils. It has a specific gravity 0*9734, and 
boils at 87° to 88 °. 

DIANTHUS PERFUMES.— See “ Carnation.” 

DIGITRONELLOXIDE. — Java critonella contains a com- 
pound, C 20 H 34 O, which Spornitz {BericMe, 47, 2478) has named 
dicitronelloxide. It boils at 182° to 183° at 12 mm., has a specific 
gravity, 0*920 at 20° ; optical rotation, — 4° ; and refractive' 
index, 1*4918., 

DIGTAME BLANG, OIL OF. — ^The oil known as essence 
de diciame Wane oit calament, which was distilled in Oran, Algiers. 



]:es lecn examined by Schimmel cO Co, (Beport, October, 1906, 84). 
It is in all j'rcbabilit}’' derived from Amaracus dictammis, one of 
the Labial (E, The oil is of a pale strav yellow colour, with a 
strong odour of pulegone, which is present to the extent of about 
85 per cent. The oil has the following characters ; — 

Specific gravity 


Optical rotation 

. -f 6° 

Acid value .... 


Ester value .... 

. 20-9 

Ester value after acetylation 

. 80 

It probablj' contains borncol and menthol. 


bark of Dicj/j^elU'inn caryophyllatuin, one of the Lauraceoi, found 
in Bi’azil. jdolds about 4 per cent, of a pale yellow oil having a 
pow’erful odour of cloves and containing much eugenol. 

DIETHYL SUGGINATE.— See “ Ethyl Succmate.” 

DIHYDROGARVEOL.— Dihydrocarvcol, CjoHigO, is a natural 
constituent of caraw^ay oil, and may be prepared by the reduction 
of carvone. It is an oil of agreeable odour, which, when pre- 
pared in as j)ure a state as possible from caraw^aj’’ oil, has a 
specific gravity, 0-937 ; optical rotation, — 6° 14' ; refractive 
index, 1-4S3G ; and boiling point, 225°. Prepared artificially 
by treating 20 grams of carvone in 200 c.c. of absolute alcohol 
wdth 24 grams of sodium, it has a specific gravity 0-927 at 20°, 
and refractive index 1-4817. It exists in both optically active 
varieties, according to the optical activity of the carvone from 
which it is prepared. 

DIHYDROGARVEOL AGETATE.— This ester has been 
identified in American oil of spearmint. 

DIHYDROGARVONE.— This ketonic compound, of the 
formula CioHigO, is found to a small extent as a natural constituent 
of caraw^ay oil, and is prepared artificially bj’- the oxidation of 
diliydrocarveol by means of cliromic acid in acetic acid solution. 
It is an oil having an odour recalling that of menthone and car- 
vone, and has the following characters : specific gravity, 0-930 ; 
boiling point, 222° ; refractive index, 1-4711 ; and optical 
rotation, — 16°. 

DIHYDROGUMINIG ALGOB-Oh.— Schimmel cO Go. {BericJit, 
April, 1904, 53 and October, 1904, 41) isolated an alcohol from 

p 177 12 


gingergrass oil' wliicli boiled at 226° to 227°, and had a specific 
gravity, 0*951 ; optical rotation, — 13° 18' ; and refractive index, 
1*4963. Tliej’’ termed this dih 3 ’'drocuniinic alcohol. It had an 
odour recalling that of a mixture of linalol and terpineol. It 
has now, however, been shown by Semmler and Zaar {Bericlite, 
44, 460) to be identical vdth perillic alcohol {q.v). Elze {Clmn. 
Zeit., 1910, 34, 1175) has claimed more recently to have isolated 
15 per cent, of the true dihydrocuminic alcohol from German oil 
of spearmint. This had a specific gravity 0*9539 ; and optical 
rotation, — 30° 15'. It yielded a naphtltyl-urethane melting at 
146° to 147°, and when oxidised jdelds an aldehyde, cUliydro- 
cuminic aldehyde, which forms a semicarbazone melting at 
198° to 199°. These figures are so close to those of the correspond- 
ing ones for perillic alcohol as to make it probable that Elze’s 
body is also identical with the last named, and is not dihydro- 
cuminic alcohol. 

DIHYDROCUMINIC ALDEHYDE.— The essential oil of 
the wood of Hermmdia peltata contains, according to ScJmnmel c& 
Co. [Bericht, April, 1915, 54), this aldelij'de, CioHj^O. The same 
body is present in the oil from the leaves of Pcrilla arguta, a 
Japanese oil known as Shiso, and is now known as perillic aldehyde, 
and as its constitution is apparently decided, and is not that of 
dihydrocuminic aldehyde, it is probable that the latter does not 
actually exist in the essential oils mentioned. 

DIHYDROFARNESOL.— Verley {Bull. Soc. Ghim. 1924, 35, 
606) claims to have synthesised a new sesquiterpene alcohol, 
wliich he names diliydrofarnesol. It is an amber-coloured oil 
having an odour resembling cedarwood. Its constitution is 
CHa : C(CH3)(CH2)3.C(CH3) : CH(CH2)2CH(CH3)CH2.CH20H. 

Earnesol is oxidised to farnesal, and tliis is converted into a 
glycidic ester, which on reduction jdelds dih^^'drofarnesol. 

DIHYDROIONONE. — ^The isomeric ionones jdeld two dif- 
ferent dihydroionones on reduction. These bodies are of no 
practical importance in perfumery, but are of great value in 
establishing the identity of the isomeric ionones (g'.'W.). 

found in the essential oil of Monardafisiulosa by kliller {Circular 4, 
1918, University of Wisconsin). 

DILEM OIL. — A name given to Java patchouli oil. (See 
" Dhelum ” and “Patchouli.”) 



DILL-APIOL. — This body is a constituent of East Indian, 
Spnnisli, and Japanese dill oils. It is isomeric with ordinal}^ 
parsk-;\' apiol, differing from it only by the relative 

jioshions of the side chains. It boils at 285° ; has a specific 


gra.vitv. T1G4 at ; and refractive index. 1-5278 at 25°. Iso- 

dill-apiol, a second isome]' of ordinary apiol. is found in the essential 
oil of Piper acntifolhnv . 

DILL, OIL OF. — The essential oil distilled from the seed of 
Av.c'Jmm gravcolcns is known as oil of dill. The plant is indigenous 
to central and southern Europe, but is found in many other 
localities. A plant growing largely in India has been described 
as AnetJium soica, but the botanical difference between the plants 
is not yet settled. The odour of dill oil is similar to that of caraway 
oil, with, however, a distinct difference. It is a mixture of 
limonene and carvone, mth traces of other bodies, but the carvone 
is present in less amount than in caraway oil. European diU oil 
has the foUovdng characters : — 

Specific gravity . . ' . 0-895 to 0-918 

'Optical rotation . . . 70° to -f 83° 

Refractive index . . . 1-4830 to 1-4900 

Carvone . . . . 30 to 60 per cent. 

Indian dill oil always has a much higher specific gravity, this 
figure usualty varying between 0-945 and 0-970. Its optical 
rotation is + 40° to + 50°. This oil contains a body, C12H14O4, 
isomeric with ordinary apiol from parsley oil, and which has been 
named dill-apiol. J. C. Umney (P. tf? E. 0. R., 1910, 290) has 
examined an African dUl oil which was distfiled fi’om plants grovm 
from Enghsh seeds. Its characters were substantially identical 
vffth English oil. Japanese dill oil appears to be produced from 
the same seed as the East Indian oil. 

CH2.C(0H)(CH3)2, is an isomer of phenjd propyl (hydrocinnamyl) 
alcohol. It forms crystals melting at 21°, and boiling at 225°. 
It is prepared by the interaction of zinc methide and phenylacetyl 
chloride. It has an odour recalling that of narcissus, hj’^acinth 
and lilac, and is one of the rarer, but higlil}’' prized, sjmthetic 

DIMETHYL-HEPTADIENE-OL.— This body is one of 
most recentty synthesised odorous compounds, formed by the 
condensation of mesityl oxide and bromopropyl acetate. It is an 




oil, boiling at 78° to 80° at 18 mm. It jDOSsesses an intense odour 
of cedarwood, and yields an acetate having a similar odour (Bogert 
and Slocum, American Perfumer, xviii., 12, G21). 
DIMETHYL-HYDROOUINONE.— This body, CcH 4 (OCH 3 ) 2 , 

the dimethyl ether of hydroquinone, is a ciystalline bodj^ 
meltmg at 5G° and boiling at 205°. It has an odour of the new- 
mo^vn haj^ type, and blends well with coumarin in flov^er odour.s, 
and is an excellent fixative. 

DIMETHYL-OCTENE-OL. — This alcohol re.sults from the 
interaction of acetobutanol and ? -butyl magimsium iodide. It 
boils at 103° to 108° at 12 mm., and yields an acetate having a 
fine floral odour. An isomeric alcohol re.sults from the condensa- 
tion of aceto-propanol and f-am 3 d-magnesium iodide. It boils at 
107° to 109° at 12 mm., and both it and its acetate have a fine 
odour resembling benzoin (Bogert and Slocum, American Perfumer, 
etc., xviii., 12, G21). 

oil of Bhimea halsamifera and several of the xanthox^duni oils 
contain a small cpiantity of this ketone, of the formula CcHo 
(C0CH3)(0H)(0CH3)(0CH3). It is an odorous crystalline sub- 
stance, melting at 82° to 83°. 

ether is a natural constituent of the essential oils of Armica 
moniana {Annahn, 170, 3G3) and Eiqmioruim iriplinerve. It is 
an odorous oil having a specific gra\dty 0-991 at 20° ; refractive 
index, 1-5134 ; and boiling point, 249°. 

DINITRO-BUTYL-ot-CRESOL methyl ether.— 

This is the “ musk ambrette " of commerce. It melts at 85°. 
{Vide “Musk.=’) 

DINITRO-BUTYL-/77 -XYLENE.— The acetyl derivative of 
this body is ketone musk. It has a rich musk odour, and melts 
at 134° to 135°. {Vide “ Musk, Artificial.”) 

one of the least common artificial musks, known as “ aldeltyde 
musk.” It is a crvstalline compound, melting at 112°. {Vide 
“ Musk.”) 

comparative^ rare artificial musk {vide “ Musk ”). It is a cr^'-stal- 
line body, melting at 110°. 

DIOSPHENOL. — Diosphenol, or buchu camphor, OioHigOg, 
is a phenolic ketone, occurring naturallj’- in certain of the buchu 



leaf oils. It is a crystalline substance having the follo^Y^ag 
characters : melting point, 84° ; boiling point, 232° ; and optical 
rotation, + 0°. It has been artificially prepared by Semmler and 
:\Iackenzie {BericJiie, 1906, 39, 1158) by oxidising oxymethylene- 
menthone and inverting the resulting diketonc vdth caustic 
alkali. Cusuiano {Att. B. Acad. d. Lined, 5, 22, ii., 1913, 569) 
has also prepared it artificially by treating dibromo-menthone 
with caustic alkali and saturating the resulting liquid with carbon 
dioxide. Diosphenol, usually in the form of buchu oil rich in the 
ketone, is of value when used in very small amoimt in odom’s 
where a suggestion of black currant flowers and fruits has been 
introduced. It also gives a characteristic tone to flavouring 
essence of black currant. Diosphenol has also been prepared from 
piperitone (q.v.). 

DIPHENYL-KETONE. — ^This body is generally known as 
benzophenone {q.v.). 

DIPHENYL-METHANE. — Diphenjd-methane CgHg-CHa 
OgHg is a very valuable synthetic perfume. Its odour is very 
powerful, and resembles that of geranium leaves, so that, in 
common with diphenyl oxide, it shares the name “ artificial 
geranium.” It is a hydrocarbon, and therefore very stable in 
the presence of free alkali, so that it is of considerable value in 
soap perfumery. It is a crystalline compound melting at 26° to 
27°, and boiling at 261°. It is prepared by the action of zinc 
dust on a mixture of benzyl chloride and benzene, or by the 
condensation of benzene with formic aldehyde in the presence 
of a small quantity of sulphuric acid. 

DIPHENYL OXIDE.— This body CgHg.O.CeHg is a crystal- 
line compound which has come into considerable vogue as a 
synthetic geranium. Its odour is strongly geranium, with a 
suggestion of orange and hyacinth. It forms crystals melting 
at 28°, and boiling at 258° to 259°. It was originally prepared 
by Gladstone and Tribe by the distillation of phenol-alummium. 
It can be prepared by the dry distillation of copper benzoate, or 
b3’' digesting diazo-benzene sulphate with phenol. This body is 
a good example of the fact that bodies are produced by the 
chemist without their odom* values being realised, unless the 
chemist happens to be a perfume expert. This body was discovered 
in 1899, and the chemist who prepared it reported that “ it has 
an indescribable orange-bice odour, but has not found any 
practical application.” It was not until about fifteen years later 



tliat its geranium odour was noticed, and it then raj)idl 3 ’- became 
a commercial iiroduct. (See also La Parfumerie Moderne, 1923, 51.) 

DIPTERYX ODORATA. — ^Thc highly fragrant seeds known 
as Tonkin or Tonka beans are derived from Dipicryx odorata and 
DlpteryxoppositifoUa, large trees of the natural order Leguminosui, 
natives of Cayenne. The former grows principallj’- in Guiana, and 
the latter in Brazil. In British Guiana the tree is known by the 
natives as Kuswam. It grows (according to SaAver, “ Odoro- 
graphia,” vol. i., p. 132) plentifully in some localities, e.specially 
above and on the islands in the rai)ids of the Esc[uibo River. The 
beans contain a fixed oil, which, when expressed, contains a 
certain amount of the perfume of the bean, and Avhich is highly 
esteemed as a hair oil by the native.s. Tliis, it is suggested, ma}^ 
be the origin of the formerly Avell-known (so-called) hair restorer 
known as balm of Columbia. The tree also gi’ows in I\Iartinicjiue. 

According to Albes {American- Perfumer, 1916, 10, 278), the best 
beans come from the region between the Caura and Cuchivero 
rivers, in eastern Venezuela, where the soil seems to be most 
favourable for the groAvth of the Tonlca bean tree. The trees are 
not usuallj* found in groves, but groAv singly, though small clumps 
arc occasionally met Avith. The gathering of the nuts is thus all 
the more difficult and arduous. CultiAmtion of the tree has been 
attempted in Trinidad and other parts of the West Indies, but 
as it takes from ton to tAvelve j'ears for a tree to come into bearing, 
this has apparentlj" discouraged the planters, and the Avild product 
is still depended upon to supply the markets. The crops seem to 
bo A’-cry irregular. As a rule, there does not seem to be more than 
one good crop in three 3 ’ears, production in the interval being so 
small that it hardily pays to collect the beans. 

In Venezuela the tree is knoAvn as sarrap>ia, the men engaged 
in the collection of the seeds being called sarrajneros. Ciudad 
Bolivar is the centre of the Tonka bean industry. 

Birds, especially of the parrot family, frequently cause con- 
siderable damage. Thc}* feed on the small immature fruit of the 
trees in the months of October and November, long before the 
beans are ready to bo gathered. Where these birds have eaten 
the ground is strovai A\dth fruit only claAved, and then aAAdcAvardlj" 
dropped, or perhaps AA’ith just a small piece bitten off. 

About the beginning of February the sarrajoieros begin to 
organise their expeditions to the interior to collect the beans. 
For tAVO or three months thereafter the Caura River is animated 
AA’ith boats of every kind and description, some of them carrying 



entire families on their w&y to the districts where the trees are 
found. As soon as a suitable place has been found, ranchos or 
huts are built, which are to be the sarrajneros’ homes for perhaps 
two or three months. Once the fruit of the trees in the vicinity 
of the ranchos has been gathered, the men go farther into the 
forests, sometimes taking their supplies with them and remaining 
absent for a week or two. 

The fruit of the Tonka bean tree resembles a mango in appear- 
ance ; it has but little pulp, wliich is sticky and tasteless, but 
edible. The seed (or bean) is covered vdth a hard furrj* substance. 
After a sufficient quantity of the fruit has been gathered, it is 
taken to some open place, where it is further treated. The hard 
shell is carefully crushed between two stones, and the single 
oblong seed removed and dried in the sun. These dried seeds are 
the Tonlva beans of commerce as they are sold to the merchants 
and exporters in Ciudad Bolivar. By the end of May or the 
beginning of June the crop is completed. 

Before the beans are exported they go through a process of 
crystallising by being steeped in strong rum or alcohol. Casks 
open at one end are filled vdth the beans to within about a foot 
from the top. The rum is then poured in until the cask is full, 
when it is covered by layers of gunny bags. After twenty-four 
hours the rum not absorbed is rim off, and the beans are spread 
out to dry in a exurent of air. When first taken out, the beans are 
of dark brovm colour and are swollen with the absorbed fluid. On 
drying they shrink and become covered with coumarin crystals. 

The tree reaches a height of 60 to 90 feet. The pods each contain 
one seed, shaped like an almond, but larger, and covered vdth a 
black shiny skin. When the seed is ripe, the seed pod does not 
open, as is usual with leguminous plants, but, when detached from 
the stem, rapidly acquires a powerful aromatic odour suggestive, 
when very dilute, of new-mown hay. This is due to the gradual 
development of about 3 per cent, of coumarin {q.v.), which may be 
seen in white crystals beneath the skin of the seed and between 
the lobes. The comparatively large amount of fixed oil present 
in the seed acts as a fixative, and prevents the coumarin from 
evaporating more than slowly, so that the beans retain then odour 
for a very long period. The beans are often found to be covered 
with a crystalline layer of coumarin, wliich is either natxual on 
account of age, the coumarin having been gradually volatilised 
from the centre to the surface, or, by their having been steeped 
in rum and then laid out to dry as above described. 



To prepare coumarin from the natural source the finely cut up 
material is boiled with 80 per cent, alcohol, the alcoholic solution 
filtered and concentrated, and the concentrate is mixed "with four 
times its volume of boiling water. The solution is filtered through 
wetted filter paper to remove fat and oil, and then set aside to 
cool. The coumarin then crystallises out, and may be purified 
b}’^ recrystallising after dissolving in hot water and shalcing vith 
animal charcoal to decolourise. The so-called “ Angostura " beans 
are the larger and more esteemed, the “ Para ” beans being 
smaller and of less fine odour. {Vide “ Coumarin,' and ” Liatris 

anatysis of essential oils embraces the determination of as many 
characters as pos.sible of the oil to be examined. Ob^^.ousl5’■, the 
greater the number of characters determined, all of which are 
compared with the knovm characters of aiithentic oils, the greater 
is the chance of coming to a correct conclusion as to whether the 
oil examined is genuine or not. This state of facts, however, is as 
well known to the dishonest adulterator as to the honest chemist, 
and the former is always endeavouring to keep a step in advance 
of the latter in order to confuse and mislead him. Endeavours 
are made to make mixtm'es which shall have the same specific 
gravity, optical rotation, refractive index, and other general 
characters as a pure essential oil has. It is ob^nous, however, 
that the greater the number of such characters to be determined, 
the less the chance of the adulterator deceiving the analj’st is. 
Hence the necessity of multiplying the number of analytical 
characters to be determined to the greatest possible extent. This 
is most satisfactorily achieved by subjecting the oil to fractional 
distillation, and so separating the oil into fractions boiling at 
different temperatures, and therefore containing different con- 
stituents, and' determining all the usual characters on all the 
fractions so obtained. Whilst a skilful adulterator may success- 
fully imitate all the usually determined characters of an essential 
oil as a whole, it is a practical impossibility, except in very rare 
cases, for him to so compound an oil that, when it is sej)arated 
into numerous fractions, all the fractions shall have the same 
characters as the corresponding fractions of the genuine oil. 

In fractionatmg an oil, the character of the oil must be taken 
into consideration in determining the method of distillation to be 
employed. Many oils can be fractionated by distillation at 
ordinary pressure in either an ordinary Wurtz flask or in a three- 



bulb flask, which- effects a rather better separation. Further 
still, heads of various forms may be used, which effect a still better 
separation of the various constituents. Other oils must be distilled 
under reduced pressure, the pressure varying according to the 
nature of the constituents of the oil. But, whatever the conditions 
of fractionation, it is- absolutely essential that the}^ should be 
identical in the case of the sample under examination and the 
standard sample with which it is being compared. 

To exemplify the value of this method of examinmg essential 
oils, the following examples may be quoted ; — 

The VTiter (E. J. P.) and Bennett have examined suspected oils 
of peppermint with the following results. 

A pure American peppermint oil gave the follovung results, the 
fractions being collected in quantities of 12-5 per cent, as distilla- 
tion proceeded : — 


Specific gravity. 


Rofractivo index. 




- 10° 




— 14° 




— 16° 




- 20° 

• 1-4640 


0-912 ! 

- 23° 




1 - 23° , 

1 1-4615 



- 34° I 

1 1-4630 



___ j 


An oil which was suspected, and finallj’- found to be adulterated 
vith the artificial ester triacetin, was distilled under identical 
conditions, and the fractions examined, vdth the follomng 
results : — 


Specific gravity. 


Refractive index. 


— 15° 




— 15° 



- 14° 



— 16° 




— 20° 















Without, discussing the characters of any fractions but tlie last, 
it is obvious that the very liigh specific gravity' and the very low 
refractive index pointed at once to adiilteration with a high 
boiling liquid, of high specific gravity and a refractive index 
which, considered with the other characters, indicated the jDresence 
• of an aliphatic body. Samples of sandalwood oil which, on the 
examination of the oil itself, gave no definite indications of 
adulteration, were similarly distilled fractionally. In this case 
nine fractions, each of 10 jjer cent., were collected, the remaining 
10 per cent, being left as a residue in the distilling flash. A pure 
normal sample gave the following values : — 


iSiJccific gravity. 


lU'fractive index 



- 18° 




— IT 




— 1G° 




— 15° 




- 15° 




; - 14° 



0-981 ' 

1 — 16° 




’ — 18° 

‘ 1-5083 


1 0-978 

— 22° 


A suspected sample gave the following results when separated 
into identical fractions under identical conditions : — 


Spooific gravity. 


Potation. I 


Pefractivo index. 




- 5° ; 





- 5° ' 




- 4° 30' 




1 — 4° 30' : 




; — 5° 50' 




' - G° 




: — 8° 



0-981 . 

— 10° 10' 




- 14° 


The great difference in the optical rotation of the fractions 
at once reveals the presence of an adulterant. (See also under 
" Lavender Oil ” for the fractionation of spike lavender oil.) 



This method of examining essential oils is invaluable, and where 
there is some abnormality which renders the oil suspicious, but is 
not in itself sufficient to condemn it, fractional distillation will 
generally decide whether the oil is pure or not. 

tion of essential oils may be conveniently divided into two sections, 
the first invoMng the scientific principles of steam distillation, and 
the second dealing with technical considerations, mainly consisting 
of the correct ' conditioning of the raAv plant material before 
distillation, and its subseq^uent treatment. 

- It is first advisable briefly to deal with , the more imijortant 
theoretical aspects of the operation of steam distillation considered 
apart from the complications wliich arise in the winning of the 
oil from its natural source. These theoretical aspects deal with the 
phenomena obtaining in the distillation of completely immiscible 
liq^uids, in this case water and the essential oil, which, for con- 
venience, is considered as a single substance. 

The basic law on which the whole science depends is that 
enunciated by John Dalton in 1802. Dalton found that, when 
two or more gases or vapours which do not associate or react 
chemically wfith one another are mixed, each gas exerts the same 
pressure as if it alone were present, and that the sum of the 
“ partial ” pressures is equal to the total pressure exerted by the 

It is necessary thoroughly to grasp this conception, and it may 
assist if it be stated in another way, viz. : The volume occupied by 
a mixture of gases or vapours is equal to the sum of the volumes 
which the component gases or vapours would occupy at the same 
temperature and pressure. 

The saturated — i.e., not superheated — ^vapom’s of liquids which 
are completely immiscible with one another foUow Dalton’s law, 
the vapoxu’ pressure of the mixture being the sum of the vapour 
pressures of the constituents of the mixture, and it is important 
to note that the total pressure is not influenced by the relative 
amounts of the constituents, i.e., water and essential oil. 

If a mixture of immiscible liquids be distilled, the temperature 
at wlficli boiling takes place, in the absence of superheating, is 
that at which the sum of the vapour pressures is equal to the 
external pressure on the system {e.g., the atmospheric pressure). 
Bach liquid, considered separately, is consequently boiling at a 
lower temperature than it would in the absence of the other 
liquid, and this temperature is the same for all the constituents. 



The vapour coming from such a boiling mixture contains all the 
constituents in proportion by volume to the relative vapour 
pressiu’e of each, and the distillate contains all the volatile 
ingredients of the original mixture. 

Steam DisiUlaiion at Ordinary Pressure. — If and P,, are the 

vapour pressures of two immiscible liquids A and B at i ° — 
c.g., water and essential oil — the two substances will distil over 

in the proportion ^ by volume of vapour. If D„ and are the 

respective vapour densities at the boiling point of the mixture, 
the relative quantities b,y weight W„ and will be expressed 
by : 

W P D 
Wt p,d; 

The molecular weight of a substance is equivalent to twice its 
vapour density, i.e., M = 2D ; hence we can VTite the equation : 

W„ _ P„M„ . 

W, - P,M„ ’ 

vliencc it follows that the mixed vapour will consist of ; 

‘ P„ + P„ 

If we consider 1 litre of the mixed vapour, this will contain 
1 litre of the vapour of each component — according to Dalton’s 
law — at its particular partial pressure, and the weight of each of 
these will be respectively : 

0-0896 X M X 273 X P 
2 X 760(273 + /.) 

Prom this we can calculate, with sufficient accuracy for our 
purpose, the amount of water that is necessary to steam-distil 
over a given quantit,y of a substance. Thus in the case of benz- 
aldeh 3 ’-de, wliieh is the chief constituent of oil of bitter almonds, 
its molecular weight is 106, its vapour pressure at 100° C. is 
61 mm. ; consequent^ the partial j)ressures of water and benz- 
aldeh 3 ’-de at atmospheric pressure and 100° are given b 3 >' : 

760 X 760 

P'„ X 760 

P'„ + P', 760 + 61 

= 703-5 for water 

P'i, X 760 

P'a + 'P'b 

61 X 760 
760 d- 6i 

56-5 for benzaldeh 3 '‘dc, 




the two partial pressures, 703-5 and o6-o, totalling to the atmo- 
spheric pressure, 760. Siibstituting in the second equation quoted, 
we get : 

W„ _ __ 18 X 703-5 _ 68 

Wi MftPf, ~ 106 X 56-5 “ 32’ 

that is, the distillate will consist of 32 per cent, of benzaldeh 3 ’'de 
and 68 per cent, of water. 

The statements made above refer to steam distillation carried , 
out under ordinary atmospheric pressure. Other pressures, 
either greater or less, may be emplo 3 >-ed, as also ma 3 ’^ be super- 
heated steam ; further, the oil itself may be superheated, pro- 
vided it is not deleteriousl 3 ’- affected b 3 '^ such treatment. Generall 3 ^ 
the ejffect of increasing the temperature or the pressure is to 
increase the proportion of essential oil relatively to the water ; 
hence, these alternatives may be usefuUy employed Avhen dealing 
with stable bodies, but they are quite unsuited to the more 
delicate essential oils, especially those containing esters or 
aldehydes in any considerable proportion. For such, the use of 
diminished pressure and low temperature is advisable, provided 
the duration of the distillation be not thereby undul 3 '^ prolonged. 

Distillation ivith Superheated Steam. — ^We vdll first consider the 
effect of increasing the temperature of the ingoing steam. If 
water be boiled in a boiler, the temperature of the steam varies 
with the pressm-e, and if the steam thus generated be allowed to 
issue from the boiler into a still worked at some pressure below 
that of the boiler {e.g., atmospheric), the temperature of the 
steam drops ovdng to the work done in expanding. The table on 
p. 190 indicates this drop in temperature in passing from the 
given boiler pressures to atmospheric or one-tenth atmospheric 

The di'op in temperature ma 3 '^ be calculated b 3 ’^ means of 
Zeuner’s equation : 

pv = BT — Cp”, 

where B, C and n are constants, and ^=38-11; ■» = 0-25 ; 

p = the pressm'e in atmospheres ; v = the volume in cubic 
metres per kilogram ; T = temperature in degrees centigrade. 

If the steam in a boiler at temperature T^, absolute pressure p^, 
and volume be released into a still at Tg, p^, v^, respectively, 

= BTj - Cpi" BTg - Cpa”, 




Ti - T. = i (j.,- - p,»). 

Thus, if a boiler gauge register oC lb. per square inch, coiTespond- 
ing to 5 atmospheres absolute pressure, and the steam be injected 
into a still at normal atmospheric pressure, from the above table 
we find ; 

152-2 — To = 38-11 (6°-= — 
whence To = 133° C. 

Similarl}’-, if 2h — one-tenth of an atmosphere, then To = 116° C. 
Thus the temperature of the steam drops from 152° to 133° or 

Boiler pre'^sure, i 
lb. per pq. incli.^ 






Temperature af 

one atmosphere. 

ter expansion to 

one-tenth atmo- 


0 : 


100° c. 

100° c. 

83-3° C. 




14 ' 




















84 1 




98 ; 


144-8 ! 


112 ! 


147-9 ! 


126 i 


150-7 i 



Thip is tlie reading on the boiler pressure gauge, and docs not include the 
14 lb. duo to the atmosphere. 

116 when injected into ci still under atmospheric j^i'^ssure or 
one-tenth of atmospheric presstire respectively. In spite, of this 
drop in temperature, the steam contains more heat than it would 
if it had been generated under ordinaiy pressure — for instance, 
by boiling water in the still itself. In this latter instance, the 
temperature would be 100° C. instead of 133° ; hence the steam is 
said to be superheated or unsaturated. Steam may also be 
superheated by passing it through pipes heated by an external 
source of heat, and a much greater degree of superheat may be 
obtained in this mamier, both these devices merely serve the 
purpose of enabling the steam to transfer more heat than it 



otherwise would. The use of superheated steam has another 
advantage, that there is less condensation due to radiation, 
the superheat of the steam causing any condensed water to 
evaporate ; so long as liquid water exists in the still, the advantage 
of the superheating is lost. If all condensation of steam is pre- 
vented, the higher temperature of the superheated steam tends 
to increase the proportion of oil in the distiUate ; the same effect 
may be obtained by heating the oil to a temperature above that 
of the ingoing steam. • 

■ Steam Distillation under Increased Pressure. — ^As an alternative 
to either of these methods, we may conduct the distillation under 
pressures higher than atmospheric. This is done by interposing 
a weight or spring loaded valve between the still head and the 
condenser ; the method is not, however, in common use. 

The effect of the pressure in the still is reflected in the folloAving 
figures obtaining for benzaldehyde : 





- 5 ^ atmosphere 

45-3° C. 

22-5 per cent. 

1 s 


31-4 „ 





38-2 „ 

It will be seen that, whereas the proportion of benzaldehyde is 
increased, the increase in the temperature to which it is sub- 
mitted is very considerable ; this for many substances is 

Steam Distillation under Diminished Pressure. — In order to 
reduce the temperature of the distillation, diminished pressure 
may be resorted to, this, as is indicated in the table above, also 
results in the percentage of the less volatile constituent, e.g., ben- 
zaldehyde, being diminished ; there is a further drawback, 
inasmuch as there is considerable difficulty in condensing the 
vapours produced. For essential oils of a delicate nature, e.g., 
lavender, neroli, the method is to be recommended, but in view 
of the technical difficulties involved, it is not usual to resort to 
pressmes below one-tenth of an atmosphere. 

Steam distillation -with superheated steam under diminished 
pressure also offers advantages. • 

The Heat of Distillation. — ^The amount of heat-^and hence fuel — 
necessary for the steam distillation of a given quantity of an 
essential oil can be roughly calculated, but it is necessary to know 


P E B F U M E R Y 

the ainountj the vapour pressure at 100° 0., and the molecular 
weight of each constituent of the essential oil. The amount of 
steam necessary for each constitixent has first to he ascertained ; 
this can he calculated from the molecular weight of the substance 
and its vapour pressure at 100° C., as has already been shown. 

From the figures thus obtained, the amount of heat necessaiy 
to vaporise each ingredient, including the water, can be found, 
tlie total heat being the sum of all these. The heat of vaporisation, 
H, may be calculated from the change of vapour pressure with 
change of temperature, using the formula : 

(?P 1-985 T2 

Jtl ==: — ^ * 

(IT P ’ 

where T is the absolute temperatiu’o at ijressure P, and dP tlic 
small rise in pressure caused by the small rise in temperature dT. 

Thus, in the case of C 3 mieme, which has a boiling point of 
174° C. — i.e., (174 + 273)° absolute — at the normal pressure of 
7G0 mm. : for ever}^ 1 mm. increase in fZP, there is an increase of 
0-057° in dT, and the heat of vaporisation at atmospheric pressure 
is given b^" 

H = 



1-985(174 + 273) 


calories per molecule. 

Experimentally, the value has been fomid to be about 2 per 
cent, lower, i.e., 8978 calories per molecule. dividing this 

value b}’- the molecular weight of cjmiene (134), the heat of 
vaporisation for 1 kg. is given as 68. 

The following data have been published concerning the heat 
of vaporisation of bodies vdiich occur in essential oils : — 

Heat of vaporisation. 

_ . 



One kilogram. 

One kilogram 

Acetophenone . 

203-7° C. 


9-3 X 103 

Anethole . 



10-6 „ 

Benzaldelyde . 



9-2 „ 

Cymene . 



9-0 „ 



68-1 . 

10-2 ., 




9-4 „ 




9-6 „ 



Dry Distillation . — few essential oils can be diy distilled, 
i.e., without water or steam, at ordinary pressure without under- 
going serious decomposition, on accoxmt of the high temperature 
that it is necessary to employ. In order to avoid this high tem- 
peratm'e, resort may be had to the use of diminished pressure, or 
as it is commonly termed, a vacuum. 

The problem now involves a consideration of the distillation of 
liquids miscible in all proportions. Only the simplest case vdll be 
dealt with here, namel}^, that of a mixture of two liquids which 
do not associate or react with one another and wliich, in conse- 
quence, foUow Dalton’s law. 

If Ya and be the vapour pressures of two such liquids A and 
B, and these be mixed in the proportion of one molecule of A to 
n molecules of B, then the partial pressures and of the two 
substances are such that : 


• and P,, = 


1 l+n 

The total vapour pressure P of the mixture is given by ; 
100P=:M,P, + (160-M,)P„ 
where is the molecular weight of A. 

By means of this formula it is possible to calculate the vapour 
pressures of mixtures of two substances at any pressure. Quite 
accurate results are obtained, except in the case of liquids which 
associate with one another ; these are, however, apparently of 
rare occurrence in essential oils. 

Wlien a mixture of two non-associating, miscible liquids is 
heated to boiling, the vapour which arises is richer in the more 
volatile component than is the liquid ; hence, as distillation pro- 
ceeds, the proportion of the less volatile component increases in 
the liquid until all of the more volatile has been removed. (The 
rnore volatile component is, of course, that having the lower 
boiling point.) It follows that the vapour has a higher proportion 
of the more volatile component, and if this vapour be con- 
densed and subrmtted to a fresh distillation, a further separation 
of the mixture into its two components is similarly effected ; by 
repeating this series of operations a sufficiently large number of 
times, a more or less complete separation may be effected, and tliis, 
in effect, is the action of a fractionating column. 

Fractionating columns are only resorted to in the case of 
essential oils, when it is desired to isolate some particular con- 
stituent or to remove midesired bodies, and it must be borne in 
mind that the repeated boihng and condensing, upon wliich the 
p. 193 



action of sucli columns depend, tend deleteriously to affect the 

The ” Winning ” of Essential Oils . — The considerations set out 
in the preceding sections concern the oil after it has been released 
from the plant in u'hich it occurs in the natural state. When the 
oil has to be distilled out of the plant, a further factor is involved, 
namely, the rate at which the plant parts with its essential oil. 
This rate may bo so slow that the other factors, such as vapour 
pressure, are swamped complete^, and it is therefore of prime 
importance to reduce as far as possible the “ lag ” thus occasioned. 
In order to accomplish this, it is necessary to submit the plant to 
some suitable breaking-up process, but in some instances, such 
as geranium, lavender, rosemaiy, the lag is so small that it can 
be neglected and no preliminary treatment given to the plant. 
The treatment varies vith the nature of the material ; thus berries 
may be crushed, seeds and roots ground, w^ood chipped, twigs and 
branches cut, and so on. When submitting the raw material to 
any preliminaiy treatment, it is well to bear in mind that exposure 
to heat and air tends to cause loss of oil through evaporation and 

Two methods of distillation are videty practised, namely, 
distillation by boiling with water (water distillation), and dis- 
tillation bj^ the injection of steam (steam distillation). The former 
is employed on account of its convenience and the simplicity of 
the necessary apparatus, but the latter, v'hich in general gives 
the better product, is employed in the larger distilleries almost 

The apparatus may be constructed of almost any convenient 
metal, copper being usually preferred ; w'ood is also often employed 
for the still body. The precise shape and size of the still is not of 
great impoidance ; cylindrical stills are the most common. The 
material to be distilled is usually supported on a perforated false 
bottom, in order to keep it from direct contact vith the hot 
bottom or steam coils, as the case may be, such contact tending 
to cause destructive distillation, with the consequent production 
of evil smelling-bodies. Instead of a perforated false bottom a 
gauge basket is sometimes employed, the spent charge being 
removed by lifting the basket out of the still after taking off the 

The vapours coming from the stiU are condensed by passage 
through a spiral coil immersed in a tank of running cold water, 
or by means of special condensers, such as the “ Ideal,” in wliich 



the vapour is caused to pass between narrow annular spaces 
formed by fixing, conccntricall}^ one tube inside another of 
slight!}’ larger diameter, a wire being wound spirall}' in the space 
between tlie two tubes. 

The liquid issuing from the condenser consists of a mixture of 
oil and water ; usually the oil is lighter than water, aiid in course 
of time floats out — ocfcasionally, however, it or some fraction of it 
is heavier and sinks ; the two la3'ers are sciiaratcd automatically 
by means of “ essenciers,’’ which consist of vessels having overflow 
tubes arranged at suitable heights. In the case of some oils, 
considerable difficulty is experienced in obtaining a good separa- 
tion of oil and Avater owing to emulsification, the Avater remaining 
cloud}’, even after standing many hours. There are three common 
methods for dealing AA’ith this difficulty : (1) retm-ning the cloudy 
AA'ater to the stiU instead of suppl}’ing fresh Avater or steam 
(cohobation) ; (2) extracting the Avater Avith an immiscible 

solvent, such as benzene ; (3) passing the AA'ater through some 
material AAdiich Avill absorb the oil, such as kiesolguhr or saAvdust, 
and then subsequently steam distilling the mass. 

When the oil has eventually been separated from the mass of 
the Avatcr, it should be dried by filtering or by setting aside in a 
cool place until clear, placed in Avell-closcd, suitable packages, 
e.g., bottles, tinned copper or tinned iron containers, and stored in 
a cool place ; careless treatment of the oil may result in rancidity, 
lack of sAA’eetncss, or bad colour. T. H. D. 

DISTILLED WATERS. — A certain number of essential oils 
contain sufficient highly aromatic constituents which are soluble 
in Avater to such an extent that they impart to the distillation 
AA’ater an odour which makes the Avater sufficiently aromatic to 
be of considerable value to the perfumer. In general, hoAvever, 
the situation of the distillery and the conditions of the distillation, 
coupled AAith economic considerations, such as the disproportionate 
freights for the conveyance of a comparatively cheap article, are 
such as to make the trade in such aromatic Avaters either impossible 
or unremunerative. It is, of course, only a feAv oils Avhich yield 
distillation waters of any value. Where the process is possible, 
distillation waters Avhich contain dissolved essential oil, and which 
are not saleable as such, are, as far as possible, returned to the 
still so that a further loss of oil, which would take place if fresh 
Avater Avere used, is thus avoided. The principal distilled waters 
which form commercial articles are rose water and orange flower 
water. Such waters are usually sold under a conventional name 

195 13-2 


as to concentration, such as aqua rosas triplex.” Such terms 
are more or less arbitrary, as they do not indicate that, for example, 
3 lb. of flowers have been distilled for 1 lb. of the water, but that, 
for example, it is an early fraction of the distillation water, so 
that considerable dilution has not taken place. It is obvious that 
the distillation water and the essential oil itself will not have 
identical odours, as their odour is not due to identical constituents. 
For example, phenyl-ethyl alcohol is a regular constituent of the 
rose flower. This alcohol is comparatively soluble in water, so 
that it is substantially absent from otto of rose (the essential oil 
of the rose), whilst it is responsible tor the characteristic odour of 
rose water. Apart from the two waters mentioned above and a 
very few others, such as cherry laurel, the bullc of so-caUed 
aromatic waters are made by dissolving a very small amount of 
essential oil in a little alcohol and pouring this into a large volume 
of water, which is weU agitated and eventually filtered, if necessary, 
with the aid of filtering powder. (See also “ Rose Water ” and 
“ Orange Flower Water.”) 

Gujmt {Jour, de Plmrm. et de CJiivi., vii., 1916, 13, 37) has 
investigated the cause of the green discoloration which often 
takes place in perfumed and medicinal waters. The follovdng are, 
according to Schimmel c& Co. {Report, 1916, 39), Guyot’s con- 
clusions : — 

“ The coloration is due to an aerobic microbe forming colomiess 
clusters of rod-hke organisms, 4 to 5 p. long and 0-5 p. wide, which 
are colomed by basic aniline dyes and methyl blue, and assume 
the Ziehl and Gram colorations. This microbe is different from 
Bacilhis liquefaciens fluorescens and from most water bacteria 
producing green fluorescence. It produces a green non-fiuorescent 
coloration. It also differs from Bacillus pyocyaneus as well as 
from Lesage’s baciUus. The new microbe appears to be able to 
exist vdthout giving off the green coloiu’ ; its colour -forming 
properties are dependent upon extraneous surroundings and the 
composition of its cultivating solution. Oxidising media and 
oxygen favour the development of the green coloration, while 
reducing substances weaken it and make it disappear entirely. 
Light has a favourable influence on the development of the green 
colour. Zinc acts as a reducing substance ; this is the reason why 
green coloration does not take place with orange flower water 
stored in zuic vessels. An alkaline reaction of the Hquid favours 
the development of the microbe. 

“ The green colom’mg matter evidently belongs to the group of 



aurantiaclilorines ; it is insoluble in alcoliol, methyl alcohol, ether, 
chloroform, and benzene, but dissolves in water. To isolate the 
colour, undyed wool is immersed in the liquid when the colour is 
precipitated on tlie wool. If the wool is treated with diluted acids, 
the green colour is converted into a brick-red one, soluble in 
alcohol, methyl alcohol, ether, chloroform, and benzene. If this 
solution is neutralised, the red colour is once again converted into 
the crecn colour, soluble in water. Cherr3'’ laurel water never 
shows green coloration. No decrease in odour is noticeable in 
the waters owing to the change involved by the green coloration ; 
on the contrary, with orange flower water, for instance, the 
opposite effect maj’’ be observed.” 

Juillet {Rourc-Bcrlraml Fils, Bvlhtin, October, 1013, 22) has 
carried out an investigation on the methods of preserving distilled 
waters and preparing them in a sterile condition. The follovdng 
is an outline of his historical resume of tlie question : — 

These waters are exceedingly unstable preparations ; their 
alterations are sometimes of a physico-chemical order (evaporation 
of certain active principles, oxidation of essential oils, etc.), some- 
times of a biological nature (attacks by fungi or algse). Conse- 
quentl 3 ^ the question of their preservation has for a long time 
occupied the attention of pharmacologists, and, wdiile not pre- 
suming to recapitulate here all the history of the problem, it 
seems to me of interest to mention its main outlines. 

At the beginning of the last centmy there was at first a belief 
(Bahoff and De 3 'cux) in the transformation of the essential oil 
into mucilage, a fact which appeared to be demonstrated to the 
authors by the observation of the presence of “ mucilage ” in the 
watery extracts obtained artificially by dissolving an essential oil 
in water. 

Soubeiran was the first to recognise the organised structure of 
these supposed mucilages, wliich Biasoletto shortl 3 ’' afterwards. 
(1832) classified among the algaj of the germs’ Hygrocrocis. Later, 
L. Marchand (1878 and 1883) and other observers showed that 
these Hygrooroois are fungi, the abnormal forms of which are the 
result of the special conditions of existence to which they are 
subject in the watery extracts. The study of these micro- 
organisms was the subject of investigations carried out by Tulasne, 
de Barry, Thuret, Bornet, and van Tieghem ; and in 1896 
Barnouvin, returning to the question, classified them in order of 
importance among the fungi, the bacteria and the algfe. 

The fungi, by far the most frequent, had first been classed in 



^ the genus Hygrocrocis ; but it is well recognised at the present 
day that the latter reallj’' comprises different genera, the characters 
of which are profoundly modified by the composition of the media 
in which the plants live. The most abundant and the most 
frequent is Penicillmm glancum, then come Aspergillus and 
Sterigmatocyslis sioecies ; the group of the Demaiia is also very 
largelj’^ reinesented by various species of Gladosporium, Dematium, 
AUernaria, to which must be added Gephalosphermm, Fusarmm, 
Mucor, etc. Man}’- of these fungi may occur under these con- 
ditions as yeast-lilce forms, and even may only affect this form in 
certain watery extracts. 

The bacteria are, as a rule, of the genera Leptotlirix, Micrococcus 
and Bacillus, with numerous chromogenic species {B. auraniii, 
B. fluorescens) capable of communicating to the distilled waters 
in which they grow the coloiu' of their pigments. 

The algas are unicellular, and belong to the genera Protococcus, 
Hemaiococcus and Goccocliloris. 

These various organisms may, moreover, coexist in one and the 
same water. But, whether they are alone or associated, they 
ahvays provoke profound modifications in the distilled waters 
infected by them. 

The changes of a physico-chemical order necessarily vary with 
the natm-e of the active principle predominant in the water. 
Thus cherry laurel water may lose by evaporation a portion of 
its hych'ocyanic acid, whilst by oxidation its essential oil may be 
converted into benzoic acid ; under the same influence the 
essential oil dissolved in orange flower water is converted into 
acetic acid, and cinnamic acid is constantly present in cinnamon 

Numerous attempts have been made to remedy these incon- 
veniences, and proposals have been made, one after another, for 
filtration, chilling, heating, sterilisation by Appert’s method, 
IDreservation in full bottles, well corked and in cool dark places, 
the addition, often unsatisfactory, of alcohol, etc., means more or 
less palliative, the effects of which are often contradictory and 
always insufficient. 

Juillet describes in detail the best method of sterilising the 
stills used, and shows that filtration through Chamberland filters 
is of extreme value in rendering these waters sterile, and, if they 
are kept under suitable conditions after having been sterilised, 
they will remain unchanged for a considerable time. For details, 
the original paper should be consulted. 



DITTANY OIL. — ^Tlie herb Ciinila origcincides, one of the 
North American Lahiatcc, jnelds 0-7 per cent, of a reddish-bro'mi 
oil resembling thj-me in odour. It has a .specific gra^fity 0-91.5, and 
contains about 40 per cent, of phenols, probably mostty tlijunol. 

DJAhlBOL LEAF OIL. — ^The leaves of Psidiuni Guajava, 
one of the Myrtacen:, a tree indigenous to tropical America, yield 
about 0-36 per cent, of essential oil of specific gra-vity about 1-069, 
and boiling at 237°. Scliiminel cO Co. have distilled some leaves 
from Santiago do Cuba, and obtained 0-2 per cent, of an aromatic 
oil hamng tlie following characters : — 

Specific gravity .... 0-9157 

Optical rotation . . . . — 10 ° 5 ' 

Refractive index .... 1-4964 

Acid value . . . . .2 

Ester value . . . . . 6-4 

DOREMA AMMONIACUiM.— See “ Ammoniacum.” 

DOREMONE. — This body is a ketone of the formula 
Ci 5 H 2 cO> occurring in the essential oil of ammoniacum. It has 
a specific gravity 0-8765 at 20° ; optical rotation, -{- 3° 30' ; 
refractive index, 1-4716 ; and boiling point about 150° at 12 mm. 
On reduction with sodium and alcohol it j-ields the corresponding 
alcohol, doremol C 15 H 27 OH, which has the following characters : 
specific gravity, 0-870 ; optical rotation, + 3° ; refractive index, 
1-4713 ; and boiling point, 145° to 150° at 12 mm. It is present 
in the oil in the form of its acetic ester. The ketone, alcohol and 
ester are all odorous liquids. 

Dorypliora sassafras have been found by Penfold {Jour, and Proc. 
Royal Soc. N.S.W., Iv., 270) to jdeld up to 0-85 per cent, of essential 
oil of a deep yellow or brovm colour, with a marked odour of 
safrol. Two samples were examined, one from leaves gathered 
at hlonga, the other from Currowan. They had the characters 
given in the table on p. 200 . 

DOUGLAS FIR OIL. — ^This oil requires a good deal of 
further examination. The reports made by Brandel and Sweet 
and by Schorger on oils stated to be derived from the leaves of 
the Douglas pine, and botanicaUy described as Pseicdoisiiga 
taxifolia, indicate an oil of no particular perfume value. Schorger 
gives the following as the approximate composition of the oil : 
a-pinene, 25 per cent. ; /?-pinene, 48 per cent. ; dipentene and 
limonene, 6 per cent. ; furfural, traces ; esters, 6-1 per cent. ; 



free borneol, G-5 per cent ; and a green oil of unknown 
constitution, 3 per cent. 

According to Henry and Flood {Proc. Roy. Irish Acad., Ma 3 ’', 
1920) this tree is Pseudotsziga glauca, whilst the Oregon Douglas 
fir is the true Pseudotsuga taxifolia. These authors give the 
details of tlie examination of the oils distilled from the leaves of 
both trees grown in England, by C. T. Bennet, who reports as 
follows upon them. The oil from the leaves of the Oregon Douglas 
fir was distilled from 50 lb. of the leaves from trees growing at 
Buckhold, Berks. The jdeld was 0*11 per cent., and the oil had 
the following eharacters : specific gravity, 0-87G ; optical rotation, 
— 7° ; refractive index, 1*4835 ; and ester content, 12*4 per cent. 
He stated that the ester value was 'much lower than that of the 



Specific gravity 



Optical rotation 

-{- 16° to + 22° 

+ 28° 

Refractive index 



Ester number 



Safrol .... 

G0-G5 per cent. 

30 per cent. 




Pinene . 



Sesquiterpene . 





3*5 „ 

Eugenol methyl ether 


Colorado Douglas fir oil, but that the odour was much more 
fragrant. The oil contains dipentene or limonene, but no, or onl.y 
traces of, pinene. An api^reciable quantitj’- of geraniol was 
separated on fractionation, and it is to this that the aromatic 
odour appears prineqjally to be due. By acetjdation 31*5 per eent. 
of alcohols was indicated. Born 3 d acetate somewhat masks the 
geraniol odour of the oil. Citral is present in traces. The oil from 
the Colorado Douglas fir was distilled from leaves from trees 
grovm in East Liss, Hampshire. The 3 deld was 0*31 per cent, of 
an oil having the following characters : specific gravity, 0*905 ; 
optical rotation, — 4G° ; refractive index, 1*4717 ; and esters, 
as born 3 d acetate, 34*5 per cent. The terpenes present consist 
mainly of pinene. The odour is due principally to the bornyl 
acetate present. (See also “ Pine Needle Oils.”) 

called Borneo camphor tree is a native of Sumatra and north-west 



Borneo. Camphor as first kno'mi in this country (Arabic Kafur, 
Sanscrit Kajntm = a pure white substance) was brought from 
the land kno'rnr as Kaisur, the present Sumatra, and was the 
product of Dryohalanops Camphora, a splendid forest tree growing 
in abundance in Borneo and on the west and north-west coasts 
of Sumatra. This substance, however, is now known to be borncol, 
and not true camphor. According to Sawer (“ Odorographia,” 
vol. i., p. 334), the borneol can only be obtained b}’’ the destruction 
of the trees, all of which do not contain borneol. IMany of them 
only contain an essential oil which has not yet developed any 
borneol. Practicallj’ all the borneol obtained from these trees is 
used locally or exported to China, either for incense or embalming 
purposes. Several of the Russian june needle oils are so rich in 
borneol or its esters that competition with such oils is out of the 
fjucstion. The essential oil has a specific gravity 0*918 ; optical 
rotation, + 11° ; and refractive index, 1*4885. Oils of low 
specific gravity have been deprived of borneol. - 

DUODEGYL ALCOHOL. — This body has the formula 
CH 3 (CH 2 )io CHoOH, and is used in minute proportions in rounding 
off floral odours. It is a liquid boiling at 257°, crystallising at low 
temperatures, and melting at 14°. It is also knovTi as lauric 
alcohol. Its specific gravity is 0*831 at 24°. 

DUODEGYL ALDEHYDE. — See under “ Aldehydes, Higher 

most popular toilet perfumes — probablj- the most popular — in the 
world. It is not, of course, intended to give formuloe for any 
perfume in this work, but the general characters of this almost 
universally used water may be indicated. The original eau de 
Cologne was in all probability actually invented in the towm of 
Cologne b}’- one Jean-Marie Farina, who was born at Sainte jMarie 
jMajeure, in Italy, and went to Cologne to trade in perfumes, and 
invented this famous blend in 1709. Another version of its 
original manufacture is that it was first placed on the market by 
one Paul de Feminis in Milan, and was afterwards made in 
'Cologne from 1690. The secret was then passed on to his 
nephew, Jean-Antoine Farina, who started manufacturing it in 
Paris. IVhichever version is correct, there is no doubt that from 
-the commencement of the eighteenth century eau de Cologne has 
been a very popular perfume, and many rival manufacturers, both 
in Cologne and elsewhere, have carried on its manufacture. The 



trade name “ Farina ” proved somewhat of a stumbling-block 
to rivals to the original maker, but they found it easy to import 
members of the Farina family to Cologne, and so became entitled 
to use the name. Endless lawsuits have taken place in regard to 
the matter, and it is not very easy to say whether any maker 
to-day uses the original recipe. Le ]\Iaout satirically wrote the 
follovdng quatrain on the “ Farina ” position in Cologne 

Ils etaient deux alors : ils sont mille ajourd’ hui 
Sur ses temps primitifs le doux progi'es a lui, 

Et cliaque jour le Eliin vers Cologne charrie 
De nombreiix Farinas, tous ‘ seal,’ tous Jean-Marie. 

Eau de Cologne is in substance the product of Italian essential 
oils, mixed with one or two others, which certainly are not 
German. It is so delicate a perfume that only the finest alcohol 
should be used for its preparation— so much so, that this fact has 
given rise to the name “Cologne sp)irit,” which indicates the 
liighest grade of alcohol for perfumery purposes. The finest Eau 
de Cologne is that produced, not by the mere mixing of the 
ingredients, but hy distilling the alcohol with most of the ingre- 
dients, and adding certain ingredients after the distillation. The 
longer the perfume is allowed to mature — up to one year — the 
better it vill be. Hundreds of formulse have been pubfished for 
this perfume, but the follovdng is sufficient to indicate its general 
characters. The bulk of the ingredients, in which bergamot oil 
should prevail, and which include lemon and orange oils, with a 
httle lavender oil and orris root, are macerated vdth alcohol for 
several days, and then carefully distfiled without the apphcation 
of naked heat. To the distillate neroli oil, a very small amount 
of rosemary oil, and a trace of a fixative such as benzoin, are 
then added, and the whole allowed to mature for as long as 
possible. Where a cheaper eau de Cologne is desu’ed, the oils are 
merely mixed Avith the alcohol, without distillation, often in the 
form of terpeneless oils. Numerous formulae, which as a rule 
are merely indicative, as obviously valuable trade secrets rarelv 
leak out, will be found m any of the text-books of practical 
perfume making. 

EGLANTINE. — This well kno^vn “ fancy ” p)6rfume is in- 
variably based on one or other (or mixtures) of the three esters — 
methyl phenylacetate, butyl (or isobutyl) phenylacetate, and 
isobutyl benzoate. 

ELECAMPANE OIL. — ^The root of Inula Helenium, a plant 
of the natural order Comjoositce, yields from 1 to 3 per cent, of a 



semi-solid essential oil, having an odour vliich recalls that of 
ladanuin. This oil liquefies at from 30° to 45°, and has a specific 
gravity, 1-015 to 1-03S at 30° (melted) ; optical rotation, + 123° 
45' ; refractive index, 1-5221 ; acid value, 6 to S ; ester value, 
160 to ISO ; and ester value after acetylation, 199. The oil 
consists almost entirely of an anhydride, named alantolactone, 
^'15^20 02> ^^so known as helinin. This is a crystalline compomad, 
melting at 76°, and boiling at 275°. 

ELEMI. — See “ Canarium Eesins.’' 

ELEMOL. — ^This substance is a crj’stalline sesquiterpene 
alcohol, isolated from the essential oil of Manila elemi, by Schimmel 
cb Go. It is the principal ingi-edient of elemi oil, to which it owes 
its fixative properties. 

Jarnsch and Fautl {BericJile, 1923, 56, 1363) have shown that 
clemol is a bicyclic sespuiterpene alcohol, which is isomerised to a 
liquid alcohol by benzo5dation. They term the crystalline body 
a-elemol and the liquid body /9-elemol. Pure a-elemol CisHogO 
forms fine needles melting at 46°, and boiling at 142° to 143°" at 

10 mm. /5-eIemol has a specific gravity 0-9419 at 18° ; refractive 
index, 1-5070 at 18° ; and boiling point, 143° to 144° at 10 mm. 

ERIOSTEMON CROWEI, OIL OF.— According to Pen- 
fold and Morrison {Jour, and Proc. Roy. Soc. N.S.W., Ivi., 227) 
the leaves and terminal branchlets of this plant (previously 
described as Crowea salnjna) yield about 0-4 per cent, of essential 

011 having a safrol-like odour. The oil has the foUov-ing 
characters : — 

Specific gravity . . . 1-109-1-124 

Optical rotation . . . + 0° 

Refractive index . . . 1-5302-1-5321 

The oil contains a little pinene, but contains about 90 per cent, 
of a phenol ether, which has been named croweacin. Two pre- 
parations had the following characters : — 

Boiling point at 10 mm. . 



Boiling point at 766 mm. 



Specific gravity 




Optical rotation 

+ 0° 


Refractive index at 20° . 




Its formula appears to be C11H12O3. 



ERYNGIUM CAMPESTRE, OIL OF.— The essential oil 
of Eryngium campesire, an umbelliferous plant’ growing in the 
South of France, is a pleasant smelling liquid, somewhat reminding 
one of oil of musk seed. It has {SchiinmeV s Report, October, 1905 , 
73 ) the foUo'v^dng characters : — 

Specific gravity .... 0’904 

Optical rotation . . . . — 5 ° 42 ' 

Refractive index . . 1*4852 

Ester value ..... 10*5 

ESTERS.- — ^The esters, as a class, are amongst the most 
important of the odorous constituents of essential oils. An ester 
is a combination of an alcohol "with an acid, the combination being 
brought about by the elimination of water. For example, ethyl 
alcohol and acetic acid combine in accordance with the follovdng 
equation, •^'liich is typical : — 

C2H5OH + HOOC.CH3 = C2H5OOC.CH3 + H2O. 

Ethyl alcohol Acetic acid Ethyl acetate AVatcr 

If the alcohol be dihydric, two molecules of acid will react 
with one of the alcohol, or if the acid be dibasic, then two molecules 
of the alcohol •wfil react •with one of the acid, and so on. Thus, 
glycerine bemg a triliydi'ic alcohol, 03115(011)3 can combine with 
three molecules of acetic acid, formmg the triacetic ester, triace- 
tin 03115(0.000113)3. Or, again, succinie acid, being dibasic, 
02H4(000H)2 forms diethyl succmate, 03114.(000.02115)2, with 
two molecules of ethyl alcohol. 

Esters are prepared by the interaction of the alcohols and acids 
at an elevated temperature, the reaction frequently being assisted 
by the presence of such bodies as anhydrous sodium acetate, 
which either acts as a catalyst or as a dehydrating agent. The 
reaction is, however, more complete if the acid anhydride is 
employed instead of the acid itself. Thus : 

2 R.OH -k O(OOR') = 2R.O.OOR' + HgO, 
where R is the radicle of the alcohol and R' that of the acid. 
For other methods of formation, such as the use of acid chlorides, 
ordinary text-books on organic chemistry should be consulted. 

Many essential oils contain considerable quantities of esters. 
For example, oils of wintergreen and sweet birch are actually 
mixtures of about 99 per cent, of the ester methyl salicylate vith 
about 1 per cent, of other substances. Lavender, bergamot and 
geranium oils are tjqDical oils wlficli owe their odour principally 
to the presence of esters. In most cases where an essential oil 
contains esters, one particular ester predominates, but small 



quantities of subsidiary esters are usually associated with it. 
Actually it is impossible to determine the amount of each ester 
separatel3’', so that it is the conventional practice to retirni the 
esters in an analysis calculated from the saponification value (see 
belov,’) in terms of the predominatmg ester. For example, the 
expression that lavender oil contains 40 per cent, of esters means, 
in fact, that if all the esters were truly iinalyl acetate, the amount 
would be 40 per cent., whereas, in fact, there may be 38 per cent, 
of true Iinalyl acetate and 2 per cent, (more or less) of other esters. 
The fact that the determination of esters is a comparatively easy 
one^ to make has caused an exaggerated value to be placed upon 
the esters in certain essential oils. Tliis is a tendency amongst 
analysts wliich is difficult to combat. Where a given constituent 
can be accurately determined in a natm-al substance, the deter- 
mination maj’- be of the highest importance in assisting iii deciding 
whether the substance is pure or adulterated, but it does not, of 
course, follow that the value of the substance is in direct pro- 
portion to the easily determined constituent. It is the failure to 
sufficiently distinguish these proportions that has led to an over- 
statement of the value of esters by those who maintain what is 
commonly called the “ ester theory.” 

It is customary — and rightly so — to assess the value of certain 
essential oils solely on the percentage of esters they contain. For 
example, bergamot oil so nearly completely owes its odour value 
to the linaljd acetate it contains that the oil is properly valued 
on the basis of its ester content. But this is far from true in the 
case of lavender oil, although the extreme advocates of the “ ester 
theory ” insist that this is the proper basis of valuation. But 
lavender oil owes its odour value to various bodies, and not to 
its Hnalyl acetate alone ; so that it is quite unsafe to value the 
oil only on this criterion. To illustrate this, it is only necessary 
to draw attention to the fact that English lavender oils never 
contain more than about 8 to 10 per cent, of esters, wliilst French 
oils contain up to 40 per cent, and over ; and there are extremely 
fine oils produced on the' Italian frontier containing only from 
25 to 30 per cent, of esters, which are of finer odom’ value than 
some French oils containing 40 to 42 per cent, of esters. Many 
factors must be taken into account in valuing such oils. The 
altitude at which lavender grows has considerable influence on 
the amount of spike lavender found in proximity to the true 
lavender and the consequent hybridisation takmg place ; and as 
spike lavender oil is practically free from esters, it is probably 



true that the ester determination affords a fairly accurate basis 
for valuing oils distilled from plants grown in the same neighbour- 

The esters in an essential oil are determined in the following 
manner. Trom 2 to 5 grams of the oO, according to the amount 
of esters expected to be present, are weighed into a small flask 
of about 250 c.c. capacity, and 10 c.c. of alcohol and a few drops 
of phenolphthalein solution added. Semi-normal solution of 
caustic potash in alcohol (of approximately this strength) is added 
drop by di-op until the free acids present in the oil are neutralised. 
Twent 3 ’--five cubic centimetres of the alkaline solution are then 
added and the liquid boiled under a reflux eondenser for one 
hour’. A “ blank ” test, that is, 25 c.c. of the alli:aline solution 
without the oil, is carried out at the same time. The contents of 
the flasks are then diluted with 100 c.c. of w^ater and titrated 
with semi-normal hj’-drochloric or sulphuric acid. The difference 
between the two titrations gives the amount of alkali that has 
been used for decomposing the ester present in the oil. Not more 
than about half the alkali used should have taken part in the 
reaction. If substantiaUj’^ more than this has been used up, the 
determination should be repeated, using either less of the sample 
or more of the allcaline solution. The number of milligrams of 
KOH used to saponif}^ 1 gram of the oil is termed the ester number. 
From this value the pereentage of esters, expressed in terms of 

M X A 

any given ester, can be calculated from the formula — = 


percentage of ester, w^here M is the molecular w^eight of the ester 
and A is the ester number. 

In order to save tedious ealculations, a table has been prepared 
by Messrs. Scliimmel ch Co. whieh gives the amount of esters for 
every value usually obtained, m terms of the usually occurring 
esters, such as linalyl acetate, citroneltyi acetate, sesquiterpene 
alcohol esters, and geranyl tiglate. (These tables are reproduced, 
by permission, in “ The Chemistrj’- of Essential Oils ” (E. J. Parry), 
vol. ii., 4th ed., pp. 323-333, q.v.) The detection of artifleial 
esters is the subject of a separate monograph {q.v.). ■ Although 
most of the following artificially prepared esters and their corre- 
sponding alcohols are described separate^ elsewfliere, the follow'- 
ing summary of their odour characters by Prins and Sclnvarz 
(P. cfc E. 0. R., 1916, 335) may be usefully given here : — 

Benzjd alcohol : Odour not very strong, slightty bitter ; 
reminds of benzaldehyde. 



Beuz3'l formate : Odour very strong, svect, pungent ; reminds 
of cinnamic alde]i3’dc. 

Bcnzji acetate : Odour strong, fruity jasmin odour ; rather 

Benz \-1 propionate : Flover odour vith a fruitj* freshness ; ver3'’ 
useful for liner soaps. 

Bcnz3'l but3’rnto : Sweet fruity odour (ajiricot). 

Benz3d valerianate : Flower odour ; reminds of the esters of 
phcjnd-etln-l alcohol. 

Phen3*I-cth3’l alcohol : lias the well-known sweet rose odour ; 
reminds of hcnz3*l alcohol. 

I?hen3’l-eth3'l formate : Has the sweet pungent odour of the 
chr3’santhemum type. 

Phen3'l-eth3d acetate : Bose odour of the red rose type ; very 
much in use. 

PEeiyd-etlyd propionate : A fine rose odour of the fruity 

Phen3d-eth3d but3Tate : A fine distinctive rose odour with a 
tinge of a leaf-lilce odour. 

Phen3d-eth3d valerianate : Has a distinctive rose leaf odour. 

Phen3d-i)roi)3d alcohol : As 3’^et rather unknown! and high in 
price ; the odour combines the rose type of phen3*l-eth3d alcohol 
with the heavier h3-acinth t3T)e of einnam3d alcohol. 

Phen3d-prop3d formate ; Has a characteristic formate odour of 
the heav3’', sweet honc3’’ and cinnamon t3^e. 

Phen3d-prop3d acetate : Kemmds of geran3d acetate, but has 
a characteristic flower odour. The cmnamon odour is not present. 

Phen3d-prop3d propionate : Has a heav3'' and sweet fruity odour. 

Phen5d-prop3d but3T:ate : Reminds of benz3d but3Tate, but the 
odour is not so pungent, though ver3’ characteristic. 

Phen3d-prop3d valerianate : Hcav3'’ odour, not ver3>- strong. 

Cinnamyl alcohol : Has the well-knowm slight h3'acinth 
odoiu- ; reminds slightly of cinnamon. 

Cinnam3d formate : Has a very sweet characteristic formate 

Cinnam3d acetate : Plo!ver odour, sweet and without cinnamon 

Cinnam3d propionate : Odour of the fruity order, 

Cinnam5i butyrate : Odour reminds of phen3d-eth3i but3uate, 
but heavier. 

Cinnamyl valerianate : Very characteristic rose odour, of the 
tea rose t3^e. 



Geraniol : The well-known rose-geranium-like odour, not very 

Geranyl formate : Eose leaf odour, as yet not extensively used, 

Geranyl acetate : Flower odour of the rose with a leaf 
odoim, not characteristic ; it is the geraniol ester chiefly in use. 

Geranyl propionate : Highly characteristic rose odour, fresh 
flower odour. 

Geranyl but 3 a’ate : Sweet odour of the fruity type, reminds 
strongly of fresh apples [reinettes cVor). 

Geranyl valerianate : Odoim fruity, reminds of the acetate, not 

Citronellol : Has a distinct, sweet characteristic rose odom-, much 
more pronounced than the odom* of geraniol. 

Citronellyl formate : A characteristic formate odour, sweet and 
more rose-lilce than geranyl formate. 

Citronellyl acetate ; Eeminds very much of phen 3 d-eth 3 d 
acetate, flne rose odour. 

Citronell 3 d propionate ; Exceedhigly sweet and lastmg rose 
odour of the heav 3 '- and Oriental kmd. 

Citroneltyl but 3 T:ate : Sweet rose odour, more flower-lilce and 
less fruit 3 ^ than geranyl but 3 a’ate, 

Citronellyl valerianate : Eose-like odour, but not strong. 

See also “ Artiflcial Esters.” 

ESTRAGOL. — Estragol, or meth 3 d chavicol, CioHjoO, is the 
principal constituent of estragon or tarragon oil, and is also found 
in anise bark, bay and femiel oils. It is a highly odorous oil of 
specifle gravity 0-972 ; refractive index, 1-5220 ; and boiling 
point, 21 G°. This body is responsible for the flavour of tarragon 
vinegar, in which the herb is used, as it is in wines of the Vermouth 
type. It is not used to an 3 ’^ extent in perfumeiy jDroper. 

ESTRAGON OIL. — Estragon or tarragon oil is an essential 
oil employed m the manufacture of wines, and in aromatic 
vmegars. It is distilled from the flowering herb Artemisia Dra- 
cuncuhis, the 3 deld being from 0-25 to 0-8 per cent, on the dried 
plant. It is a colourless or pale yellovdsh-green oil, with an odour 
recalling that of aniseed, and having the following characters : 
specifle gravity, 0-900 to 0-945 ; optical rotation, -f 2° to fl- 9° ; 
refractive index, 1-5020 to 1-5140 ; acid value, 0 to 1 ; ester- 
value, 1 to 9 ; and ester value after acetylation, about 15. Roure- 
Berhxnul Fils, however, have found a sample, distilled by them- 
selves, with the abnormal specific gravity 0-981. The oil contains 
much mcth 3 i-chavicol (estragol). 



ETHYX< ACETATE. [Magnolia oil contains a very small 
quantity of ethyl acetate CII3.COO.C2H5. It has a very fruity 
odour, but is^ very soluble and very volatile, so that it does not 
play^ a very important part in perfumery. It boils at 76°. Its 
specific gravity is 0’906 to 0’907, and refractive index 1-373. 

ETHYL-AMYL-GARBINOL. — ^This body is one of the 
isomeric octyl alcohols, of the formula CH3(CH2)4.CH(0H)(C2H5). 
It occims naturally in oil of Japanese peppermint, and has been 
prepared artificially by Pickard and Kenyon {Jour. Cham. Soc., 
1913, 103, 1923) by passing the vapour of a mixture of 145 grams 
of normal caproic acid and 180 grams of propionic acid through a 
tube charged with thorium oxide at 400°. The ethyl-ainyl- 
ketone so obtained is reduced to the alcohol by moist ether and 

The alcohol has also been synthesised by Schimmel c& Co. 
{Report, Aprfi, 1912, 102 ; April, 1913, 82). 

The following are the characters assigned to it by the chemists 
quoted : — 

Pickard and 

Schimmel & Co. 

Boilmg point 



Specific gravity 


0-8247 at ~ 

0-8276 at 15° 

Optical rotation 

Refractive index 

Melting point of acid phthalate. 
Melting point of semicarbazone . 

4- 6-79° 


-}- 6-43° 

ETHYL-AMYL KETONE.— This body, C2H5(CO)(CH2)4CH3, 
occims naturally in Erench lavender oil. It is an aromatic oil, 
having a specific gravity 0-825 ; boiling point, 170° ; and refrac- 
tive index, 1-4154. On oxidation it yields normal caproic acid. 
It forms a semi-carbazone melting at 117° to 118°. 

ETHYL ANISATE. — ^This body is a crystalline body, of the 
qrmula C6ll4(0CH3)(C02.C2H5).. It has a fine odour of chervil. 

^THRANILATE.-This ester, C5H4.(im2) 
(LUgOgHs) IS a very odorous liquid boiling at 260°. It occurs in a 
few essential oils, and is of fine neroh odour. It closely resembles 

*’• 209 14 


methyl antliranilate {q.v), but is rather sweeter and softer in 
perfume, and does not discolour so readily. It can be prepared 
artificially by the action of hydrochloric acid on ethyl alcohol and 
anthranil-carbonic acid (isatoic acid). It is useful in artificial 
neroli and jasmin. 

ETHYL BENZOATE.— This ester, C 6 H 5 .COO.C 2 H 5 , is not 
a natural constituent of any essential oil, so far as at present 
known. It is used in the preparation of artificial ylang-ylang and 
similar flower oils, and is used generally for the same pimposes 
as the corresponding methyl ester, which is known as niobe oil. 
It is prepared artificially by the condensation of ethyl alcohol and 
benzoic acid by means of hydrochloric acid. It is a sweet-smelling 
oil, which has the following characters : specific gravity, 1-0502 
to b0530 ; refractive index, 1-5050 to 1-5063 ; and boihng point, 
212 °. It is soluble in 2 volumes of 70 per cent, alcohol and in 
7-5 volumes of GO per cent, alcohol. 

ETHYL BUTYRATE. — ^Pineaj)ple essences invariably con- 
tain this most useful fruit ester, a liquid boiling at 121 °, of fine 
fruity odour. It has the formula CH 3 (CH 2 ) 2 COO.C 2 H 5 . It is 
useful in minute quantities for modif^^fing artificial rose and similar 
odours. The commercial ai-ticle consists of a mixture of isomers, 
with a boiling range from about 115° to 140°. It is never a very 
pure article. 

ETHYL CAPROATE. — ^This ester (ethyl hexoate) is occa- 
sionalty used for its fruity odour. It has a specific gravity 0-877 ; 
refractive index, 1-4075 ; and boils at 167°. 

ETHYL ^ CAPRYLATE. — ^Ethjd caprylate (eth 3 d octoate) 
CH 3 (CH 2 )cCOO.C 2 H 5 is an ester having an odour recalling that 
of secondary products of vinous fermentation. It is probably a 
constituent of oil of cognac, and is useful in modifying floral 
bouquets. Its specific gravity is 0-873 ; refractive index, 1-4171 ; 
and boiling point, 208°. 

ETHYL CINNAMATE. — ^The cinnamic ester of ethyl 

alcohol C 6 H 5 .CH : CH.COOC 2 H 5 is not often found naturally, 
but is a constituent of the essential oils of Kaempf&ria galayiga and 
Stoi ax. It is prepared artificially by passing a .current of dry " 
hydrochloric acid gas thi'ou^ an alcoholic solution of cinnamic 
acid. It is an odorous liquid, optically inactive, solidifying on 
cooling, and melting at 12 °. It has a specific gravity 1-050 at 20 ° 



refractive index, 1-5590 ; and boiling point, 271°. It is useful in 
sweet, heavy bouquets of the Oriental type, and also in eau de 
Cologne where a heavy, persistent sweet tone is desired. 

ETHYL CITRATE.— See » Esters, Artificial.” 

ETHYL-DEGINE-GARBONATE.— This new synthetic is 
analagous to the corresponding heptinc-carbonate. Its -formula 
is CgHi^.C i C.COOCjIIg. It is an oil having a “ leafy ” perfume, 
.recaUing that of mignonette, in which type of perfume it is of 
considerable value .- 

ETHYL DEGYLATE. — ^The ethyl ester of capric, or decylic, 
acid, CH 3 (CHo) 8 C 02 C 2 H 5 is a synthetic perfume, prepared by the 
esterification of capric acid, which is present in cocoa nut oil, 
with ethji alcohol. It has a floral odour and is useful in artificial 
rose perfumes. 

ETHYL FORMATE. — ^This ester resembles ethyl acetate in 
general characters, but has a rather sharper odour. It is a liquid 
of specific gravity, 0-926 ; refractive index, 1-3600 ; and boiling 
point, 55°. 

ETHYL-HEPTINE-GARBONATE.— This expensive sub- 
stance, CgHij.C ; C.COOCgHg, is one of the most recent sjmthetic 
perflunes, having what is known as a “ green leaf ” effect, espe- 
cially in the modification of the ipxixe flower effects in violet and rose 
perfumes. {Vide Amyl-heptinc-carbonate.) 

ETHYL HEPTOATE. — Oenanth 3 ^hc ether is the common 
name for this ester. It has a fragrant odour recaUing that of the 
secondary constituents of vinous fermentation. It is sold in a 
nearly pure condition as artificial oU of cognac. It is an oil 
boiling at 188°, and is used to a limited extent in the manufacture 
of artificial flavouring essences, and in artificial flow^er extracts. 
Its specific gravity is 0-871, and refractive index 1-4140. 


synthesised by Bogert and Slocum {American Perfumer, xviii., 
12, 621), possesses a fine fruity odour. The free acid wdien 
distUled under reduced pressure gives isoamylbutyrolactone, an 
oil boilhig at 131° to 134° at 12 mm., having a fine odoii of 
peaches. ' 

ETHYL LAURINATE. — ^This ester is used in very small 
quantities in the preparation of artificial flower perfumes, such as 

211 14-2 


mignonette and tuberose. It is an oil of very sweet, fruity odour, 
and of intense strength. It boils at 269 °, and has the formula 

ETHYL MALONATE. — ^Blalonic other, as the diethyl ester 
of inalonic acid is usuall}^ termed, is of great value in general 
S3nithetic chemistiy, but has also recently been recognised as a 
useful artificial perfume. Its odour is fruity, recalling that of 
apples, but much sweeter than that of the valerianic ester. It is 
prepared bj’' treating either potassium cj^'anacetate or malonic acid 
with ethjd alcohol and hydrochloric acid. It is an oil of specific 
gravit}^ 1 - 070 , and boiling at 198 °. Its formula is CH2(C0002H5)2. 

ETHYL MYRISTINATE. — This ester is a semi-solid body, 
melting at 11° and boiling at 295 °. Its formula is CH3(CH2)i2 
COOC2H5, and it is jnepared bj'- the esterification of m3n’istic acid 
and eth3d alcohol b3>- means of h3’drochloric acid. It is of powerful 
and persistent odour, and is useful both as a fixative and in 
modif3mg floral odours, especial^ violet perfumes. 

ETHYL-OCTINE-CARBONATE.— This is still an experi- 
mental S3nithetic. It is analagous in all respects to the correspond- 
ing heptine-carbonate. Its formula is CgHi3.C | C.COOC2H2. 

ETHYL OLE ATE. — ^Ethyl oleate is an ester principal^ used 
as an “ arificial ” ester for adulteration purposes. {Vide “ Esters, 
Artificial.”) It has, however, a slight floral odour, and also fixative 
properties. It is a liquid of the formula CjL7H33.COO.C2H5, 
boiling at about 340 °. 

ETHYL PELARGONATE. — ^This ester (eth3d nonylate), 
of the formula CH3(CH2)7COOC2H5, is a very fragrant oil made b3'' 
melting undec3denic acid with caustic potash, and setting free 
the resulting pelargonic acid b3’- dilute sulphuric acid. This acid 
is then esterified with eth3d alcohol in the presence of sulphm-ic 
acid, and purified b3’' fractional distillation. It boils at 100° to 
110° at 10 mm. pressure, or at 228 ° at normal pressure. It has a 
specific gravity 0 - 876 , and refractive index 1 - 4255 . 

ETHYL -PHENYLAGETATE.— This ester is formed by the 
condensation of eth3d alcohol and phen3d-acetio acid. It is a very 
sweet smelling oil with an odour recalling honey and roses. It 
is ver3'' useful in compounding artificial rose odours. Its formula 
is C6H5.CH2.COOC2H5. It has a specific gravity about 1-0366 ; 
refractive index, 1-4990 ; and boils at 227 °. 



ETHYL PHTHALATE. — As a perfume ethyl phthalate lias 
no Talue. It is, however, of considerable ser\dce as a solvent for 
artificial mnsk, and has also a fixative value. Its principal use, 
however, is as an “ artificial ” ester for the purposes of adultera- 
tion. It is a liquid of specific gravity, 1-124 ; refractive index, 
1-5020 ; and bods at 293°. One per cent, indicates, in- the usual 
method of anatysis, 1-77 per cent, of linahd acetate. Its formula is 
CgH 4 (COOC 2 H 5 )o. It is prepared by the esterification of phthalic 
acid ^vith eth}-! alcohol. 

ETHYL SALICYLATE. — ^The usual artificial wintergreen oil 
is methyl salic 5 date {q.v.). The eth}*! ester, CcHj.CHg.COOCoHs 
is a liquid boiling at 234° ; of specific gravity, 1-1372 ; refractive 
index, 1-5234 ; and optically inactive. It sohdifies at low tem- 
peratimes, and melts at 1-3°. It is an oil having a very fine vdnter- 
green odour, more dehcate than that of the methyl ester. 

ETHYL SUCCINATE. — Succinic ether has no legitimate 
use in perfumery, but is used as an “ artificial ” ester for adultera- 
tion purposes. It is an oil boiling at 216°, and has a specific 
gravity 1-044. One per cent, appears in tlie usual method of 
analysis as 2-26 per cent, of linalyl acetate. It results from the 
esterification of succinic acid and ethyl alcohol. 

ETHYL VALERIANATE. — ^This ester, C 4 Hg.COOC 2 Hg is an 
oil with a powerful fruity odour. It results from the esterification 
of valerianic acid and ethyl alcohol. The commercial article is a 
mixture of isomers, of specific gravity about 0-875 ; refractive 
index, 1-3980 ; and boding point, 135°. 

EUCALYPTOL. — ^This body, or cineol as it is more scien- 
tificaUy tei’med, is the characteristic constituent of the majority 
of the eucaljq)tus ods. There are, of course, a certain number of 
the ods of this species which are free, or practicaUy free, from this 
constituent. The eucatyptus oils which contain eucalyptol are 
used to some extent in perfumery, but rather as antiseptics than 
as pleasant odour bearers. Eucalyptol is an oxide, of the formula 
CioHigO, having a specific gravity 0-930 ; refractive index, 
1-4590 ; melting point, -f 1° ; and boiling point, 176° to 177°. 
The usual process for the determination of eucal 3 rptol in eucalyptus 
and other ods containing eucalyptol is that devised by Scammel. 
This, as used to-day, is carried out as follows. To a known weight 
(about 5 grams) of the od, from 1 to 1-5 times its weight of 
phosphoric acid, of specific gravity 1-75, is slowly added, drop by 



drop, with continual stirring, the mixture being kept cold all the 
time. The ciystalline magma Avhich results is strongly pressed 
between filter paper after as much as possible of the terpenes 
present has been drained ofi. The cr^^stalhne mass is, after 
repeated pressing, decomposed by hot water in a flask with a 
graduated neck, and the hberated eucalyptol measured off in the 
neck. There are several other methods of determination of 
eucalyptol, but the only one possessing any merits comparable 
Avith those of the original phosphoric acid method is that devised ■ 
by Cocking (P. & E. 0. R., 1920, 281), and varied by Wallcer. 
This method is a physical one, and depends on the determination 
of the freezing point of a mixture of the oil eontaining eucalyptol 
and or//m-cresol in proportions corresponding approximately with 
the molecular weights of the two substances; A stout-walled 
tube suspended by a AAire loop to the balance is used for the 
determination. Into this is AA^eighed 3 grams of the oil and 
2- 1 grams of melted or/^o-cresol. The tube is then removed from 
the balance and inserted through a bored eork into a Avide-^ 
mouthed bottle containing water, which can be heated or cooled 
as necessary. The mixture is agitated, and the sohdifying point 
noted. It is then warmed until melted, and the solidifying 
point again noted. This process is repeated until the sohdify- 
ing point becomes constant. With a pm’e or^/m-cresol melting at 
30° the folloAving results were obtained Arith mixtures of known 

eucalyptol content : — 

Per cent, of 

Freezing points (varying accordinj 


tlie nature of the admixtrrre). 

100 . 

. 65-2° 

96 . 

. 63-4°-53'6° 

90 . 

. 51-2°-51-7° 

85 . 

. 48-5°-49-7° 

80 . 

. 45-8°-47-7° 

75 . 

. 43-2°-45-7° 

70 . 

. 40-6°-43-8° 

65 . 

. 37-4°-41-2° 

60 . 

. 34-2°-37-4° 

65 . 

. 29° -33-6° 

50 . 

. 25-4°-29-8° 

45 . 

. 22-2°-26-2° 

Walker {Jour. Soc. Ghem. Ind,, December, 1923) prefers the 
use of a-naphthol to o-cresol in the freezing point determination, 
on account of the non-hygroscopic nature of the compound. This 
modification has been criticised by Cocking (P. Js E. 0. R., 1924, 
10), who states that : — 



“ (1) In the crcsineol method the freezing point is the tempera- 
ture at wiiich the solid cresineol separates from the mother liquor, 
which latter consists of a saturated solution of cresineol in a 
mixture of the non-cineol portion of the oil, and o-cresol in 
vnvarying proj)orlwns. 

“This mixhna is gjcrmaneiithj liquid at ihe icmqjeraiure of the 

“ (2) In Wallcer’s proposed modification the freezing point is 
influenced by the crystallising out of the a-naphthol in addition 
to the a-naphthol-cineol compound, and thus the mother liquor 
will consist of the non-cincol portion of the oil saturated with 
a-naphthol and •with the a-naphthol-cineol compound, the relative 
proportions of -which v'ill vary with the temperature. It is thus 
apparent that, while this modifled method may give fairly accurate 
results on oils containing from 100 to 50 per cent, of cineol, it 
cannot be relied upon, as the freezing points obtained vdth such 
oils are also given by oils containing from 0 to 50 per cent, of 

For other methods of determining cucal 3 q;)tol, see “ The 
Chemistry of Essential Oils, etc.” (E. J. Parry), vol. ii., 4th ed., 
p. 270. 

EUCALYPTUS CITRIODORA. — ^This tree is kno'UTi as 
the citron-scented eucalyptus, and is found along the coast of 
Queensland and as far south as Port Jackson. It has been stated 
to be a variety of the New South Wales spotted gum. Eucalyptus 
maculaia, but it is considered by Baker and Smith to be a separate 
species. The essential oil is well known, having been on the 
market for some years. As the tree is a tall one, the cost of collect- 
ing the material for distillation is high, and as the yield is only 
about 0-75 per cent., the cost of the oil is at present rather out of 
proportion to its perfume value as compared with other oils of 
-the same type of odour. It is so rich in citronellal that it is 
undoubtedly the best source (apart from questions of price) of 
that body, and citronellol produced therefrom is said to be superior 
to that from any other source except LepiospermuTn ciiratuin. 
And since it is possible, bj’' fractional distillation only, to raise 
the aldeh 3 '^des to 98 per cent., thej>' can be reduced directly, 
without the expense of previous separation by means of their 
bisulphite compounds. The tree has been extensively cultivated 
in private gardens in and around Sydney for ornamental pur- 
poses. In its native state it has never been found further 
south than Bundaberg, in Queensland. The oils from the wild 



and the cnltivated trees hare given the following results on 
distillation : — 




Specific gravity 



Optical rotation • 

— 1° to -f 2° 

0°to - 1-15° 

Refractive index 




Up to 95 per cent. 

95-98 per cent. 

It also contains traces of geraniol and puiene. It is far more 
dehcate in odour than any type of citronella oil. The tree much 
improves hy cutting, and if cultivated as a small tree the leaves 
can be collected at a cheap rate. Many cultivated trees have 
been found to jield well over 1 per cent., even up to 1-5 per cent., 
of oil, which is a great increase over that obtained from the wild 
trees. The small trees can be cut when they are from three to 
five years old. The cultivation of this tree on a commercial scale 
would probabl}' be exceedingly remunerative, and allow the oil 
to compete successfully with Java and Bm’mese citronella ojls. 
[Vide Bulletin No. 5, Technological Museum, Sydney, N.S.W., 

perfume-bearing oils recentl}’’ examined, and which are derived 
from raw material grovm in the British Empire, that of Eucalyptus 
Macarthuri is one of the most remarkable, and is worthy of 
very considerable attention. The oil is at present almost entirely 
consumed locally in Australia as a denaturant of alcohol for 
perfumery pm’poses. It is an oil which is extraordinarily rich 
in geranjd acetate, so much so that, by skiKul manipulation, 
gerany] acetate of 80 to So jDer cent, strength, the balance being 
principall 3 ’ free geraniol, can be jDroduced from it without acetyla- 
tion. As the species is somewhat sparsely distributed, attempts 
have been made to cultivate it in Australia, and, being one of 
the apparently stable species, the oil seems to remain constant in 
composition. There is a plantation at Emerald, in Victoria, 
started in 1911, which has given good results. A sample of the 
oil distilled by Penfold (Bulletin No. 5, Technological Museum, 
Sydney, N.S.W., 1923) from leaves of plants gro%TO at CrojMon, 
near Sj'dney, from seeds collected by Dr. Guthrie, gave the 
following results on analysis : jfield of oil, 0-26 per cent. ; specific 



gravity at 15°, 0-9274; optical rotation, +3-1°; refractive 
index, 1-4744 ; and geranjd acetate, 67 per cent. Trees grovTi at 
Longueville and Aslifield from seedlings taken from Croydon gave 
essential oils wliick 3 delded the following results on anatysis : — 

Yield of oil per cent. 
Specific gravity . 
Optical rotation . 
B.efractive index . 
Esters as geranyl acetate 
Free geraniol 



0- 9255 
+ 3-2° 

1- 4692 

74-8 per cent, 



0- 9257 
+ 3-5° 

1- 4696 

70-2 per cent. 

The trees can be cut for distfilation every year and yet produce 
their full quantity of leaf for next year’s cutting. By keeping 
them as small trees they 3 deld more fohage, and the cost of 
collection is less. Moisture is essential, but the tree vdll grow in 
poor soil, although a good soil will cause an increased yield of oil. 
The oil has been recommended as a source of geraniol, though, as 
this requires a preliminary saponification, it is probable that the 
cost would be prohibitive ; but as a source of geranyl acetate the 
tree would probably amply repay careful cultivation. 

EUCALYPTUS PIPERITA. — This species of eucalyptus 
may be of considerable commercial importance as a source of 
supply for piperitone, if this substance should, as hoped, prove 
a suitable raw material for the manufacture of thymol or menthol. 

It is (“ A Research on the Eucalyptus,” Baker and Smith, 2nd 
ed., 274) a tail tree with a fibrous bark, found round Sydney and 
in Victoria and Queensland. The account of the yield and 
characters of the essential oil distilled from the leaves and terminal 
branchlets in 1897 given by Baker and Smith {loc. cit.) has quite 
recently been supplemented by Penfold and Morrison [Jour, and 
Proc. Roy. Soc. N.S.W., Iviii., 1924, 124). 

It is pointed out that Baker and Smith gave the yield of oil as 
0-8 per cent., the oil, on distillation, yielding 85 to 86 per cent, 
distilling below 200°. Although there is no record of the quantity 
of piperitone present in this species, it could not have been more 
than 5 to 10 per cent., and this has usually been assumed to be 
the case. Many inquhies have been made by persons clearing 
their property of this species for information regarding the oil, 
and they were advised according to the foregoing results. Field 
observations made by Penfold and Morrison during the past 
few years, however, led them to suspect that the trees of this 



species growing around Port Jackson contained much more than 
the published yield of oil (0-8 per cent.), and, from the odour of 
the crushed leaves, that piperitone was present in considerable 
quantitj". Consequently, they decided to reinvestigate the matter, 
and material was collected from such places as Longueville, 
K^higai, Como, etc., with the result that field observations were 
confirmed. The leaves and terminal branchlets, cut as for com- 
mercial distillation, collected about the same period of the year, 
March-April, and weighed when fresh, yielded from 2 to 2-5 per 
cent, of oil, containing 40 to 60 per cent, of piperitone. The oils 
thus obtahied closely resembled those from E. dives, so much so 
that it is doubtful if an unlabelled specimen of each could be 
difierentiated. These results are especially interesting, as they 
confirm in a very striking manner the observation of Surgeon- 
General White made in the '' Journal of a Voyage to New South 
Wales,” pubhshed in London in 1790, that the name of “ Pepper- 
mint Tree ” had been given to tliis plant on account of the very 
great resemblance between its essential oil and that of the Enghsh 
peppermint, Manilla ‘pi-parita. Such a description would appear 
most unlikely if the oil had resembled that described by Messrs. 
Baker and Smith, where the piperitone content did not exceed 
10 per cent. These authors state, in the work mentioned, page 274, 
under Pemarks : “ In this research particular interest pertains 
to tliis species, as it was from trees of the’ ‘ Sydney Peppermint,’ 
growing where Sydney now stands, that the first eucalyptus oil 
was obtained. It was distilled by Dr. White, Surgeon to the 
First Fleet, in 1788, and it seems remarkable that they did not, 
at the time of their investigation, examine the oils from trees 
grovdng in or around Sydney as well as those from fifty to 100 
^ miles away. It is probable that the 'composition of the oil, 
described below, closely resembles that first distilled in 1788.” 

In view of the disparity between Baker and Smith’s results 
and those now recorded, Penfold and Morrison have carried out 
a considerable number of observations and experiments on oils 
obtained from this species growing in various locahties and 
altitudes, and have come to the conclusion that, apart from slight 
variations likely to be due to the influence of ecological conditions, 
there are two very distinct forms of this tree, one growing 
close around Sydney — ^say, the Port Jackson district — ^ 3 delding 
2 to 2|- per cent, of oil containing 40 to 60 per cent; of piperitone, 
and the other ^fielding only 0-6 to 0-8 per cent, of oil low in 
piperitone, but high m phellandrene and eudesmol, and containing 



up to 20 per cent, of cineol, found principally in the more moun- 
tainous districts. This latter is tentatively termed the mountain 
form, or variety “ A,” to distinguish it from the typical form. 

The type E. piperita and its varied forms are being carefully 
studied, and the final result of their observations will be dealt 
with in a later publication. Meanwhile, they prefer merely to 
direct attention to the strildng difference in the composition of 
the oils of two very distinct forms, and to the interesting nature 
of that obtained from trees grovdng at Port Jackson, the chemical 
and physical constants of which are totally different to anj-thing 
that has previously been published concerning the oil of this 

In the table particulars are given only of the oils from the Port 
Jackson trees, those from other localities being left for a later 

The oils distilled by Penfold and Morrison had the following 
characters : — 





Como. . 







Optical notation. Refractive Index, ®°™A/cohoV“ Kperitone Content, 

Per cent. 

— 64-60 

— 52-00 

— 62-75 

1 in 9 
1 in 5-6 
1 in 5-3 




These oils on distillation yielded, on an average, 40 per cent, 
distilling at 60° to 75° at 10 mm., 18 per cent, at 75° to 100°, and 
42 per cent, at 100° to 110°. 

Separation of Phellandrene and Piperitone. — The portion distil- 
ling at 60° to 75° at 10 mm., on fractionation, readily yielded 
pheUandrene of boiling point 59° to 61° at 10 mm., having a 
specific gravity at 15°/15° of 0-8467 ; optical rotation, — 93° ; 
and refractive index, 20°, 1-4729. The last fraction (boiling 
point, 100° to 110° at 10 mm.) was found to consist principally 
of laevorotatory piperitone having an optical rotation of — 57°. 
On purification through the bisulploite compound, it possessed 
the following characters : boiling point at 10 mm., 107° to 108° ; 
specific gravity, 15°/15°, 0-9386 ; optical rotation, — 10° ; and 



rofrnctive index, 20°, 1*4830. Cincol was not detected in tlie 
terpene fraction. 

The oil described bj!- Baker and Smith had the following 
characters : — 

Specific gravity .... 

Optical rotation . . • ■ — - 2*7^ 

Refractive index .... 1*4781 

Saponification value . . .11 

EUCALYPTUS STAIGERIANA.— This tree is knowji 
as the lemon-scented ironbark of Queensland. It is a medium- 
sized tree, and so far has only been found in the Palmer River 
district of north Queensland. 

The oil was referred to by Schimmel ct* Co. as far back as 1888 
{Semi-Annual Report). According to Baker and Smith, the 
dried material j'ieldcd from 2*5 to 3 per cent, of oil having a specific 
gravity 0*8715 ; optical rotation, — 38° ; refractive index, 1*4814 ; 
and containing GO per cent, of ?cei‘o-limonene, 16 per cent, of 
citral, the remainder being gcraniol, geranyl acetate, and a 
.sesquiterpene. Two samples I’cccntly examined by Penfold 
{Bulletin No. 5, Technological Mnscum, Sydney, N.S.W., 1923) 
gave the following results : — ^ ^ 

Percentage yield 
Specific gra%nt5'- 
Optical rotation 
Refractive mdex 
Citral . 

2*59 per cent. — 

0*8777 . . 0*8822 

— 34*G° . . — 26*4° 

1*4793 . . 1*4797 

28 per cent. 38 per cent. 

This oil has been said by experts to be suitable for flavouring 
confectionery in the place of lemon oil, and also to be suitable for 
denatui*ing alcohol to be used for the manufacture of ean de 

EUCALYPTUS STUARTIANA. — ^The eucalyptus oil from 
this tree has an odour recalling that of apples. It contains 
eucalyptol, pinene, and esters which have not been fully investi- 
gated. It has a specific gravity 0*916 ; optical rotation, 4*7°‘; 
and refractive index, 1*4780. 

EUDESMOL.— This compound is a crystalline body, melting 
at 80°, of the formula CisHacO, which is a sesquiterpene alcohol. 
It was first isolated from the oil of EucalyiAus pigicrita by H". G. 
Smith {Jour. Proc, Roy. Soc. N.S.W., 1899, 33, 86), and later 
examined by Semmler and Mayer {BericJite, 1912, 45, 1390), and 
Semmler and Tobias {BericMe, 1913, 46, 2026). It is a crystalline 



bod.y melting at 78°, boiling at 156° at 10 mm., of specific gravity 
0-9S84 at 20°, and refractive index 1-5160. 

EUGENIA APICULATA, OIL OF.— The Cliilian plant 
Eugenia ajnculala possesses leaves wlucli are used to a consider- 
able extent as a drug. According to ScJn7mncI tfc Co. {Rejjorl, 
October, 1910, 145), it yields 1-27 j:)cr cent, of essential oil having 
an odour recalling that of myrtle. Its characters are as follows : — 

Specific gi’avitj’ .... 0-892 

Optical rotation . . . . -{- 12° 40' 

Refractive index . . . 1-4782 

Acid value .... 5-5 

Ester value . . . .25-8 

Ester value after acetylation . 65-3 

EUGENIA GHEKEN, OIL OF— The leaves of Evgenia 
c/fcA'c;?, aplant belonging to the natural order Myrlaccce, indigenous 
to Chili, yield about 1 per cent, of an essential oil having a pleasant 
odour recalling those of sage and eucal 3 rptus. It is of a yellowish- 
green colour, and has the following characters : — 

Specific gravity .... 0-8795 

Optical rotation . . . . -{- 23-5° 

The only constituents so far identified are pinene and cineol. 

EUGENIA JAMBOLANA.— The seeds of this plant, a 
member of the natural order Myriacecc and a native of the West 
Indies, are knovTi as jambul seeds. Power and Callan {Pharm. 
Jo7ir., 1912, 88, 414) have distilled the essential oil, which is 
pale 3 'ellow in colour and ver}' aromatic. It has a specific gravity 

0-9258 at — -, and an optical rotation — 5° 42'. 

20° ^ 

EUGENIA OCCLUSA, OIL OF.— Schimmd cG Co. [Report, 
April, 1911, 123) have reported on an oil knovni in Java as “ salani 
oil.” It is distilled from the leaves of Eugenia occhtsa, the yield 
being about 0-05 per cent. Its properties are as follows : — 

Specific gra^^ty .... 0-9567 

Optical rotation . . . . — 1° 40' 

Refractive index .... 1-4681 

It contains citral and other aldehydes not yet identified. 

EUGENIA UNIFLORA, OIL OF.— According to Peckolt 
[Bericlite d. DeutscJi. Pliarjn. Ges., 1903, 13, 130), the seeds of 
Evgenia uniflora yield about 0-043 per cent, of a yellowish essential 
oil having an aromatic pepper-like odour. The leaves yield about 
0-14 per cent, of a similar oil, of specific gra'sdty 0-963. 



EUGENOL. — ^Eugenol, C 10 H 12 O 2 , is a phenol occurring in 
oils of clove, cinnamon leaf, bay, pimento, and others. It is the 
characteristic odour bearer of clove oil, in which it occm’s to the 
extent of from SO to 95 per cent. It is used to a very considerable 
extent as the rav'^ material for the manufacture of vanillin, and to 
a small extent for the manufacture of isoeugenol. Both eugenol 
and isoeugenol are necessary constituents of all carnation per- 
fumes {ci.v.). 

Eugenol is a pale yellowish oil of intense clove odour, having a 
specific gravity 1‘070 ; refractive index, 1*5439 ; and boiling 
point, 252° to 254°. It forms a characteristic benzoyl derivative 
melting at 69° to 70°, and a dii5hen3durethane molting at 107° 
to 108°. 

Eugenol in essential oils is almost invariably determined by 
absorption bj^ means of a solution of caustic soda {vide “ Phenols, 
Determination of ”). A more elaborate method, which possibl}'’ 
gives more accurate results, is that devised bj’’ Thoms, wliich is as 
follows. About 5 grams of the oil are weighed into a small beaker 
and 20 gi'ams of a 15 per cent, solution of caustic soda added, and 
then 6 grams of benzojd chloride. The mixture is well stirred, 
and the whole eventually'’ sets to a solid mass, much heat bemg 
evolved. To this mass 50 c.c. of water are added and the mixture 
warmed on a water bath until the compound is completely melted, 
the mixture well stiiTcd, and allowed to cool again. The clear 
supernatant aqueous liquid is filtered off and the cry'^stalline mass 
t-wice remelted and washed with 50 c.c. of water. The crude 
benzoyl-eugcnol is then recrystallised from 25 c.c. of hot alcohol, 
which is first passed through the filter in order to dissolve any 
benzoyd-eugenol thereon. The liquid is cooled to 17° and the 
ciystalline precipitate collected on a small weighed filter paper, 
filtered, and washed with 90 per cent, alcohol, until the filtrate 
measures exactly 25 c.c. The filter paper and ciystals are weighed 
after being dried to constant weight at 100° G. To the weight so 
ob tamed 0*55 gram is added to allow for the solubihty of the 
benzoyl-eugenol in the 25 c.c. of 90 per cent, alcohol. From this 
the weight of eugenol is calculated, the molecular weight of 
eugenol being 164, and that of benzoyd-eugenol 268. This method 
is not used, however, for commercial analysis. 

EUPATORIUM, OILS OF . — Eupatorium foaniculaceum 
is a herb knovm as dog fennel, and is distributed through the 
northern parts of America. It ynelds on distillation an essential 
oil of a golden j'-ellow colour and a pepper-like odour. Miller 



{Bull. Univ. of Wisconsin, 1914, 693, 7) lias examined a number 
of samples distilled in Alabama, the jdeld of oil _being about 
1 per cent. The principal constituent of the oil is the dimethyl 
ether of th3nnohydroquinone. Born3d acetate, borneol, linalol, 
phellandrene, and probabl3" sabinene, are present in the oil. It 
has a specific gravity 0-919 to 0-9G0 ; refractive index, 1-497 to 
1-507 ; optical rotation, — lG-7° to -}- 14-3° ; and contains from 
4G to GG per cent, of th3-moh3-droquinone dimeth3’l ether. The 
oil distilled from Enpaiorhmi triplinervc, a plant indigenous to 
tropical America and found vild in other tropical countries, is 
of similar compo.sition. 

EURYANGIUIM SUMBUL. — This plant, also known as 
Ferula Sv.vihul, possesses a highly odorous root, known as sumbul 
root. On distillation it yields 0-2 to 1-7 per cent, of a viscid dark- 
coloured oil having a musk-like odour. Its specific gravity is 
0-941 to 0-9G4 ; optical rotation about — G° ; acid value, 7 ; 
and ester value, 17 to S5. Its constituents have not 3^et been 

EURYBIA AROPHYLLA. — ^This tree is one of the natural 
order Gomposiloi, and is confined to Australia, Tasmania, and 
New Zealand. Its leaves have a very pronounced odour of musk ; 
hence its popular name the “ silver-leaved musk tree.” 

EVERNIA PERFUMES. — ^The extracts of mousse de chene 
of commerce {q.v.) are obtained inier alia from Evernia furfuracea 
and Evernia priinastri, lichens flourishing on oak and other trees. 

EVODIA oils. ^The evodia trees belong to a genus of .small 
rutaceous trees or sluaibs, mostly natives of tropical New Holland 
and the Indian archipelago. Most of the species are veiy sweet- 
scented plants. The best known are Evodia Uorlensis, a native 
of the Friendly Islands and the New Hebrides, a plant whose 
leaves are used by the natives to perfume coconut oil ; Evodia 
simplex, and Evodia Ruiaecarpa, The oil distilled from Evodia 
simplex in Reunion was found by ScMmmel <b Co. {Berichi. 
October, 1906, 83) to have the following characters ; 

Specific gravity at 15“ . . 0-8737 

Optical rotation . . . . 13° 4' 

Acid value . . . . . 2-1 

Ester value . . . - . . IQ.4 

Ester value after acetylation . . 63-3 

The oil contains methyl-eugenol and a crystalline ly^drocarbon 
melting at 81°. , - 



The essential oil distilled from the fruit of Evoclia Rufaecaiya 
has been examined hy Asahina and Kashiwald {J our. Pharm. Soc. 
Japan, November, 1915). These chemists isolated from it a 
terpene wliich they termed evodene, which is allied to the olefinic 
terpenes of which myrcene is a t3^pe. 

EXCQECARIA AGALLOGHA.— This plant, which belongs 
to the natmal order Eupthorhiaceoo is a higlily odorous tree, the 
wood being used in Dutch East Indies as a fumigant under the 
name Menengen. The heart-wood of young trees is the most 
odorous, the wood of old trees becoming almost odourless as 
resinification takes place. The constituents have not been fully 
investigated, but an alcohol melting at 85° is present in the form 
of an ester. 

EXOTHEA GOPALILLO.— An oil distiUed in Mexico from 
this tree known as copalillo oil has been examined by Roure- 
Eertrand Fils {Bulletin, 1914-1919, 138). It is a dark yeUow oil 
with an odour recalling that of linaloe oil. It had the foUovdng 
characters : — 

Specific gravitj’’ .... 0-8504 

Optical rotation . . . . + 0° 50' 

Acid value . . . .10-2 

Ester value . . . . .13*1 

The methods used for the extraction of the perfume material 
from the plant are extremely variable. The methods themselves 
are, in general, old-established in principle, but during the last 
few decades scientific investigation has been brought to bear 
upon the questions involved, and there has been a vast improve- 
ment in the methods in which these processes have been applied. 
Fifty j’-ears ago, distOlation, for example, was just distiQation, 
and that was all. The effects of time, pressure, and temperature 
were practically neglected ; esters were hardly known, and if 
they were decomposed dming the process of distillation, so much 
the worse for the resulting oil. To-day, knowledge of the characters 
of the constituents of essential oils, and of the conditions under 
which they are extracted in the most perfect condition, has 
advanced to such an extent that many raw materials for per- 
fumeiy are undoubtedly prepared in an ideal manner. At the 
same time, one has to remember that many of the plants used 
for the extraction of perfumes- grow wild, or are cultivated in 
spots far distant from large towns and under such conditions that 



the time occupied in transporting the raw material to an up-to- 
date factory in a largo town would, if such transport were pos- 
sible, cause the material to deteriorate to such an extent that the 
resulting perfume would be largely spoiled. The most scientific 
factories and apparatus can onl}- exist economieallj’ where there 
is within reasonable distance a i^lentiful suppl^y of the raw material 
to be treated. The majority of the natural perfumeiy materials 
which arc employed to-daj^ are the result of distillation processes. 
This method of production is dealt with under “ Distillation ” 

For the preparation of a certain number of essential oils, how- 
ever, distillation is not a suitable process, the oil being sufficiently 
altered by the exposure to heat and moisture to become of quite 
inferior quality. These oils arc prepared bj’- a cold process of 
expression. Still, other essential oils arc of such a delicate 
character, and are present in such minute amounts, that no process 
of distillation or expression is practicable. For this type of oil, 
ho separation is, in cfTcct, possible on a commercial scale. The 
perfume is extracted bj’- means of a solvent and marketed in 
admixture with other substances extracted at the same time, as, 
for example, in the form of absolutes, concretes, or pomades. 
For practical purposes, then, the methods of separation of the 
perfume materials from the plant may, apart from the collection 
of exudations, such as in the case of oleoresins, etc., be grouped 
in the above manner, namely, by (1) distillation, (2) expression, 
(3) extraction by solvents. Of these, as mentioned above, distilla- 
tion is treated under its own heading. 

The typical expressed oils of interest to the perfumer are those 
of lemon, bergamot, orange, and lime. 

■The bulk of the lemon oil of commerce is produced in Sicily, 
where it is prepared, practically entirely, b}’- either the Scorzeiia 
or the Epxigna methods. Almost every other process which has 
from time to time been introduced has been discarded, and the 
older processes have not been improved upon. In the Scorzetta 
process, the fruits (lemons and oranges) are cut into halves by a 
sharp knife, either longitudinally or across. If the peel after 
the expression of the oil is destined for candied peel, it is usual 
to cut the fruits longitudinally. The pulp and juice are removed 
as completely as possible. The peel is soaked in water for several 
hours, which causes the cell walls to become stiller and enables 
them to be more completely ruptured than would otherwise be 
the case, so that the oil globules are more completely discharged. 

P- ' 225 15 


The men who actually express the oil sit m front of an earthenware 
jar, across which rests a bamboo stick, which supports several 
sponges, one of which is cup-shaped. The operator presses the 
peel into the sponge vdth one hand, the other hand pressing the 
sponge. This is done several times, the peel being turned round, 
so that as much as possible of the oil exuding from the burst oil 
cells is absorbed b}'’ the sponge. Where the peel has been cut 
longitudinally, round sponges are used in place of cup-shaped' 
ones. The oil gradually collects in the jar, mixed with water, 
pulp, etc. The water is allowed to separate, and the oil is stored 
in a cold cellar, filtered, and stored- in coppers or tins. The. 
so-called Spugna method diflfcrs only from the above described in 
details. The peel is removed by three longitudinal incisions, the 
inside of the fruit remaining intact for after-Jreatment for the 
lemon juice. It is quite obvious that an essential oil prepared 
in tliis, or in similar manner, is not quite accurately described as 
an essential oil. It is really an essential oil holduig in solution 
such dissolved substances as are present m the peel, and which 
have become dissolved in the oil. Hence, all such oils contain a 
fixed non-volatile residue when evaporated on the water bath, 
consisting of such solid or semi-solid dissolved substances. 

The so-caUed Ecudle method was formerly used in Nice and 
the neighbourhood, but is hardty ever employed to-day, except in 
the West Indies for the production of hand-pressed oil of limes. 
The process consists in causing the fruits to be roUed about m 
cup-shaped vessels the bottom and sides of which are covered 
with metal (brass, as a rule) needles. The oil cells are punctured, 
and the oil, with some watery liquid, graduallj'^ collects in a 
tubular extension of the vessel, and is collected and filtered 
as usual. The “ Machine ” process is practically confined to the 
expression of the oil from bergamot fruits. The most general 
mechanical appliance used is a primitive hand-worked macliine, 
in which the round fruits are rotated between discs provided 
with either needle points or knives, suitable arrangements 
being made for the collection of the oil which exudes from 
the ruptured cells. It is obvious that in most of these somewhat 
crude processes, there must be a good deal of more or less waste 
residues. These are often worked uj) by distillation, so as to 
reduce the loss of oil to a minimum. The distilled oils, however, 
as has been indicated above, are of considerably inferior quality 
to the expressed oils, and are practically never marketed as such. 
They are usually kept separately and used to mix with the cheaper 



qualities of the expressed oil. In dealing -with these exi)ressed 
oils, it must be remembered that not only must the water be 
completely removed from the oil (which is, of course, equally 
true for distilled oils), but also the albuminous and similar matter 
derived from the fruits, and which never occurs in distilled oils, 
must be got rid of completely*, since such impurities tend to 
decompose, and impart a very unpleasant odoxir and flavour to 
the oil. (Refer also to U.S.A. Patent Specification No. 1353109 ; 
and P. c& E. 0. P., 1921, 18.) 

The solvent extraction processes may be divided into two 
princqDal classes. Of these the older is the extraction by means 
of a non-volatile solvent, such as animal fats or vegetable fixed 
oils. This method may be subdivided into (a) enfleurage, where 
only normal temperatures are employed, and {h) maceration, 
where heat is applied. The more recent jirocess of extraction is 
that by means of volatile solvents, such as petroleum ether, where 
the solvent is diiven off and the extracted perfume material, etc., 
is recovered and marketed in a concentrated form. 

The marketed products of enfleurage and maceration are the 
well-known pomades and perfumed oils, or, of course, the floral 
extracts obtained therefrom by “ washing ” with alcohol. The 
method of extracting the perfume from delicate flowers by means 
of a non-volatile fatty solvent is of considerable importance, and 
is fairly ancient and of very general application in the treatment 
of flowers. The method in which the treatment is applied differs 
according to whether the odorous constituents of the flowers are 
capable of withstanding a more or less elevated temperatmu or 
not. And again, it differs according to whether the flower 
contains the whole of its potential perfume in a directly available 
form, so that the killing of the plant tissues by means of hot fat 
is a matter of indifference, or Avhether the perfume exists in the 
form of some glucosidal or similar compound, so that as fast as 
the fat removes the actually existing perfume material normal life 
processes in the flower cause the decomposition of more of the 
glucoside uitli liberation of more perfume material. In the latter 
case it is obvious that the flower tissues must be kept alive as 
long as possible, and hot fat is inadmissible. This point is exempli- 
fied in the case of jasmm, the perfume material of which can be 
extracted either by volatile solvents or by cold enfleurage. But 
both the yield and quality are much superior if the enfleurage 
process be adopted. Mviere, following the previous work of 
Hesse, gives the following explanation of this important difference 




{La Parjwnerie Moderne, 1921, 225). It is quite clear that the 
jasmin flower contains one or several glucosidal bodies. He has 
made exjDerimcnts on the effect of a preliminaiy hydrolysis before 
extraction, and in all cases obtained a higher yield when hydrolysis 
2Dreceded extraction. It is customary to say that the enfleurage 
IDrocess yields four to five limes as much as the direct extraction 
until a volatile solvent. But it must be remembered that, when 
the enfleurage pomade is washed with alcohol, a considerable 
amount of fatty material is dissolved, so that the true perfume 
yield by the enfleurage process is not so much higher than that by 
the dii’ect extraction b}'’ petroleum ether, as is generally supposed. 
But it cannot be denied that the odour of the two products is very 
difl'erent. In the enfleurage product the presence of indol is very 
noticeable, and this is due to glucosidal decomposition under the 
influence of an enzjmie. 

Enfleurage and maceration jirocesses consist in placing the 
flower in contact with fat (usually high-grade lard or fine beef 
suet) or with olive oil, and sometimes mineral oil. It is absolutely 
essential that the fat or oil should be of the veiy higliest grade and 
as free from fatt}’" acids as possible. The essential oil of the flower 
is dissolved out by the fixed oil, wliich eventually absorbs the vdiole 
of the perfume material from the plant. The following is, briefly, 
the ju’oeess adopted in the maceration of flowers as detailed by 
Charabot (“ The Present State of the Perfume Industry ”) : — 

The fat being molted on the water bath (or the oil being 
heated), the flowers to be treated are added to it, and the mass 
is stirred to assist the extraction. The exhausted flowers are 
replaced b}'’ fresh ones until the fat is sufficiently charged with 
perfume. Eor that purpose a given weight of flowers is allowed 
for a charge of fat. The flowers, after treatment, still retam some 
of the perfumed fat. This is removed from them by pressing 
them, whilst hot, by means of presses. In this way there are 
obtained jromades when fats are emplo5’’ed, and perfumed oils 
when olive or mineral oils are used. The process is carried out 
at Grasse, jDrincipally in the case of the violet, the rose, the orange 
flower, and the cassie blossom. 

Certain flowers, such as the jasmin and the tuberose, wliich 
contain in the free state only a portion of the odorous matters 
which they are capable of yielding, must, as indicated above, 
be treated bj" the jirocess of cold enfleurage. Eat is spread on 
both sides of* a sheet of glass surrounded by a wooden frame. On 
the upper surface of this apparatus, which is called a “ chassis,’^ 



the flowers are spread. Another chassis is placed on the top of 
the one thus charged, and so on. The flowers are thus enclosed in 
chambers of which the top and the bottom faces are covered with 
fat. The fat oh the bottom surface becomes perfumed b}"- contact 
and by diffusion ; the odorous matters which escape are retained 
by the fat adhei'mg to the upper surface. 

After a certain time — tlic next da}' in the case of jasmin — the 
exhausted flowers are rei^laced by fresh ones, care being talcen 
to turn the chassis over. This operation is repeated until the 
desired concentration is obtained. If it be rccpiired to prepare a 
perfumed oil instead of fat, the chassis employed differs from that 
described above in the fact that the sheet of glass is replaced by a 
metal grid which supports a thick cloth winch is saturated with oil. 

A\hether the “ maceration ” process or the “ enfleurage ” pro- 
cess be emj)loycd, the odorous products are obtained m the form 
of pomades or perfumed oils. 

The perfume is dissolved in a vehicle, fat or oil, from which it 
must be freed. For that purpose use is made of the property, 
which the odorous compounds possess, of dissolving in alcohol, 
which property is not possessed by the fatty matters employed. 
It is suffleient to beat up the pomade with alcohol for the latter 
to absorb the perfume without cb'ssolving appreciable quantities 
of fat. i\Iorcover, the small proportion of fat retamed by the 
alcohol is eliminated by cooling the solution to a temperature 
of — 10° to — 15° C. and by subsequent filtration. The exhaustion 
of the fats is effected mechanically by means of hatleuses (beating 
machines). Several successive washings are necessary. 

These alcohol washings form the exlrait-s aux fleurs or floral 
extracts of commerce, and the exhausted fat, from which the 
greater part of the perfume material has been thus extracted, is 
sold as corjjs eimise for use in soap perfumery. The pomades are 
themselves sold under numbers, usually multiples of 12 — thus, 
flower pomade No. 12, 24, 36, or 72 ; the higher the number 
the higher the degree of concentration claimed for the pomade. 
In the same way the alcoholic washings knovm as extracts arc 
usually sold as triple or quadruple, and are, especially the “ triple ” 
extracts, frequently bottled off as handkerchief perfumes as they 
come from the manufacturer, or, blended vith other natural or 
synthetic perfumes and then marketed under fancy names. 

The extraction of perfumes by means of volatile solvents is a 
comparatively new industry, although one wliich has recently 
made, and is still making, very rapid strides. The process was first 

, 229 


suggested Robiquet in 1830j when, of. course, light petroleum 
ether was unknown in commerce. It u'^as not, however, turned 
to industrial account mitil successful experiments were carried out 
by Massignon ; but it is pre-eminently to Naudin that the process 
has developed into a successful industry on a large scale. To-day 
there are more than twenty factories in the south of France alone 
which carry on the extraction of flower perfumes by this method. 
In 1879 Naudin took out his master patent {No. 130137, French 
Patent) on a ' New Commercial Method of extracting Perfumes 
in vacuo and in the Cold.” The apparatus therem described con- 
sisted essentially of an extractor formed of a closed receptacle 
vdth a pannier for holding the flov’^ers, with a decanter and an 
evaporator. The extract was charged with the flowers and solvent, 
and the cover replaced and sealed. After contact with the flowers 
for about a quarter of an hour, that part now charged vdth 
perfume was directed b,y means of diminished pressure into the 
decanter, where the water from the flowers separates. The 
solvent eventually found its way into the evaporator by gravity. 
The solvent was then evaporated at the ordinar3^ temperature in 
vacuo, so as to avoid all heating efi'ects. The condenser was kept 
at a very low temperature by artificial means. As regards solvents, 
Naudin suggested ethyl chloride and the lighter fractions of 
American petroleum. (Interesting accounts of Naudm’s work 
will be found in the Bull. 8oc. CMm., 1882, 38, 586, and in the 
Monilcur Scieniifiq^iie, February, 1883, 174.) Naudin established 
the validity of his patent in the French Court of Appeal, but the 
expenses of the litigation nearly ruined him, and he abandoned 
the patent in disgust, and it may be regarded as the substantial 
basis of all methods in use to-da}’- in France. The essential oil and 
resins of the plant are the onl}^ perfume bearers, and in choosing 
a solvent for extraction purposes the following points have to be 
carefully borne in mind : — 

(1) It must dissolve out the v4iole of the odour-bearing sub- 
stances present in the plant. 

(2) It must be perfectly neutral and inert and have no chemical 
action whatsoever on the odorous substances. 

(3) It should dissolve as little else as possible from the plant 

(4) It must distil steadily within such limits of temperatm-e 
that the perfume material is not damaged by the heat necessary 
for distillation, and so that the perfume material should not itself 
volatilise with the solvent and so cause considerable loss. 



(5) It must leave no residue and no odour behind on evapora- 

The principle of extraction 'is more or less that of a Soxhiot 
extractor, so that the process is continuous. When the whole of the 
perfume is extracted by the sokent— very low boiling petroleum 
ether being the most suitable for nearly all purposes— -the solvent 
is recovered, and the residue consists of the essential oil, resinous 
matter, fat, wax and coloiu-ing matter. This raw material is 
usually solid or semi-solid on account of the wax and fat present ; 
hence the name “concretes.” But as the wax and fat are 
insoluble in alcohol, it is obvious that the emploj^ment of these 
concretes gives rise to considerable inconvenience, usuall}- accom- 
panied by a loss of alcohol, as perfect filtration is necessary to 
separate the insoluble waxy matters. Charabot has worked very 
successfully in the direction of removing this inconvenience. He 
gives the following brief summary of the outluies of improvements 
which lead one from the concretes to the so-called “ absolutes ” 
or “ liquid flower oils,” as they are sometimes called (“ The 
Present State of the Perfume Industry,” Paris, 1909, p. 8) ; 

“ The period at which the process of extraction of perfumes by 
volatile solvents entered into the region of industrial realities, 
some fifteen years ago, coincided exactly with the time of my first 
researches at the Sorbonne, in the laboratory of Charles Friedel, 
in the same laboratory where, first under the direction of Wurtz 
and subsequently under that of mj’' illustrious and lamented 
master, such a strenuous and glorious struggle had been main- 
tained for the definite triumph of the splendid atomic theory, 
thanks to wliich organic chemistry has produced the marvellous 
results vhich are so evident to all. The industiy of the artificial 
perfumes, on the morrow of the discovery of ionone, had just 
taken a new step in advance, and the sjmthetic jiroducts were 
begiiming to claim their place in compositions of the finest quality. 
Perfumery then had need of natural raw materials sufficiently 
powerful, and consequently sufficiently concentrated, not to be 
dominated, crushed out of existence by the chemical perfumes. 
These latter were capable of imparting, even to the most delicate 
compositions, valuable characters of originality and fixity, but 
only on the express condition that they can be sufficiently 
dominated by products derived from flowers, which are the only 
ones which can impart delicacy and sweetness. It was this 
necessity, accentuated still more by the tendency of fashion 
towards powerful and tenacious perfumes, which struck me, 



together with the inconveniences involved by the first products 
obtained by means of volatile solvents. And thus my researches 
were directed towards the obtaining of the -perfumes of flowers 
in the form of products both powerful and soluble in alcohol. 
The}'’ soon led to a satisfactor}' solution and the preparation of 
products conforming with the desiderata mentioned above. 
Since then we have been able to substitute for the first processes 
which I invented methods which are more perfect because they 
have been deduced from the accumulation of acquired knowledge 
both on the composition of the odorous matters and on their 
successive states m the plant. And these methods, made appio- 
priate to the treatment of each flower, have enabled us, by 
employing the solvents m a suitable manner, to leave the vegetable 
wax, the inodorous substance which is insoluble in alcohol, beliind, 
and to extract solely and completely the odorous principles in the 
form of products entirel}' soluble in alcohol. These products, the 
absolute fiower oils, are consequently extremely convenient to use, 
since it is only necessary to pour them into alcohol to obtain a clear 
solution of any concentration that may be desired. 

“ But, being extremely powerful products, they have a some- 
what high value, and their prices differ from one flower to another. 
In order to have for each flov'er products which are comparable 
among themselves, and which can be sold at a price which makes 
them more convenient to handle, it was most desirable that these 
products should be standardised in sirengtli and of uniformly 
excellent quality. 

” The form of liquid floiver oils is the most advantageous from 
all points of view for the utilisation of the odorous products 
extracted from plants. In addition to all the quahties enumerated 
above, the liquid flower oils possess the very important advantage 
of presenting no variation from one crop to another, since they do 
not contain, like the solid flower oils, the odourless wax, the 
proportion of wliich is essentially variable according to the 

Amongst the flowers which are regularly treated in this manner 
may be mentioned rose, orange. Jasmin, tuberose, cassie, jonquil, 
narcissus, carnation, mignonette, broom, mimosa, and "violet. 

The exact method by which the insoluble wax is removed from 
the concretes differs according to the manufacturer, but in general 
it consists of agitating the concrete vdth alcohol in suitable 
machines {batteuses) and removing the insoluble matter by 
filtration, and then cooling the filtrate to 20° below zero in order 



to cause tlie last traces of dissolved wax to separate. The 
“ absolute ” oil is separated either by removing the alcohol m 
vact!o or by salting out and separating. Attempts, partially 
successful, to remove all colour from these absolutes have been 
made by distilling the oil from the absolute. Owing to the intense 
strength of these oils, the}' are freciuently standardised vdth a 
neutral body so that thc^' are perfectly soluble in alcohol, and 
a whole series of absolutes by one maker may have identical 
strengths in relation to the finished product in which it is to be 

FACE POWDERS. — ^Toilet powders are merely mixtiires of 
certain white powders, tinted or untinted as desired, and per- 
fumed to taste. The absolute essentials of a satisfactory’' face 
powder are (1) freedom from grittiness, (2) the desned amount 
of adherence to the skin, (3) satisfactory colour and perfume. 
For the first, the most perfect grinding (where grinding is neces- 
. sary) and sifting must be employed, so that the resulting powder 
be absolutely impalpable. In order to cause the powder to 
adhere to the skin, a careful choice of the main ingredient is 
necessary, as well as the discreet employment of small quantities 
of a subsidiary substance. For example, wheat starch does not 
adliero to the skin nearly so well as does maize starch. The 
questions of colour and perfume -are, of course, matters of taste 
which do not require discussion here. 

The principal constituent of the older-fashioned, and still highly 
esteemed, face powders is starch powder, the most usually em- 
ployed varieties being maize and rice starch. The old-fashioned 
violet powder was essentially a mixture of starch and powdered 
orris root with a trace of perfume. 

These old-fashioned powders have been to a certain extent 
replaced by the more modern “ talc ” or “ talcum ” powders, 
which are based on finely powdered talc (q.v.). 

To these powders a small quantity of particularly adherent 
substances is commonly added, amongst wliicli are zme oxide, 
bismuth carbonate, subnitrate and oxychloride, zinc or magnesium 
stearates, kaolin, and kieselguhr. 

The mineral substances usually incorporated in these powders, 
apart from those above mentioned, are precipitated chalk, light 
magnesium carbonate, but scarcely baiium sulphate, as is often 
stated, except occasionally in very small quantities, as it is so 
extremely dense. 



FormulaB b3^ the hundred for these preparations are to be found 
in all the text-books on practical perfumery. (See also P, & 
E. 0. B., 1923, 442.) 



F ARNES AL. — See “ Farnesol.” 

FARNESOL. — ^This body is an aliphatic sesquiterpene alcohol, 
of the formula CiqHsgO. It occurs in the essential oils of ambrette 
seed, acacia (cassie), lime flowers, mignonette, and lilac flowers. 
In ambrette seed oil it is present to some extent as the ester of 
palmitic and other acids. In order to prepare it from this oil, the 
oil should flrst be saponifle’d, after dilution with alcohol, by 
heating it with alcohohc potash under a reflux condenser for 
eight to ten hours. The alcohol is removed by distillation, and 
the residue washed with water. The crude farnesol is distilled in 
a current of steam, and purified by conversion into its phthalic 
acid ester. It is present in ambrette seeds to the extent of about 
0- 1 per cent., associated with a little decylic alcohol. It is a fragrant 
oil of apparently very little odour, but in dilute alcoholic solution 
it has a sweet odour recalHng that of a mixtine of hly of the valley 
and cedarwood oil. ■ It has the following characters : — 

Boiling point at 10 mm. . . 160° 

Specific gravity .... 0*887 

Optical rotation .... 0° 

Refractive index . . . .1*4881 

The constitution of farnesol has been established by Kirschbaum 
{Berichte, 1913, 46, 1732), who has also prepared it synthetically 
by acting upon diliydropseudoionone with magnesium bromoacetic 
ester. The resulting hydroxydihj’-drofarnesic ester is heated with 
acetic anhj^dride and sodium acetate, when farnesic method ether 
results, from wliich farnesol is set free. (See also Ruzicka, Helv. 
Chim. Act., 1923, 6, 492, for the complete synthesis of farnesol.) 

If farnesol be oxidised by chromic acid mixture, the correspond- 
ing aldehyde, farnesal C15H24O, results. This is an odorous body 
having a specific gravity 0*895, refractive index 1*4995, and 
boiling at 174° at 14 mm. It forms a crystalline semicarbazone 
melting at 133° to 135°. Farnesol forms an acetic ester, farnesyl 
acetate, boiling at 170° at 10 mm. pressure. 

Farnesol is of considerable value in perfumery if used with 



Ku/iiclva {Joe. cit.) gives the following as the characters of the 
specimens of farnesol prepared from the sources quoted : — 

Source of farne'Ol. Specific gravity. 

Ambrette seed oil . 0-885 at 18° ' 

Xeroli oil . . 0-803 at 15° 

Citronella oil . 0-895 

Java cananga oil . 0-895 ,, 

Synthetic . . 0-891 at 20° 

(7-Nerolidol . . 0-895 at 18° 

Eefraotive index. 


1-4924 at 18° 

It is probable that some of these specimens repi-esent geometrical 

Xaef & Co. have patented the preparation of farnesol by the 
action of acetic acid upon nerolidol, or bj' the oxidation of 
nerolidol to farnesal by means of chromium trioxide and reduction 
of the farnesal (International Convention date, March 22nd, 1923). 
(See “ Xerolidol.”) 

FENCHONE. — ^This ketonic compound, of the formula 
C^ioHicO, is found in bitter feimel oil, and also to a small extent in 
the oil of Lavandula Sfoecha-s. In both these oils it exists as 
dexiro-iencliono, but is also found as Zroro-fenchone in thuja leaf 
oil. It is an oil of characteristic sharp odour, having the following 
characters : — 

Boiling point 
Melting point 
Specific gravity . 
Refractive index 
Specific rotation 


+ 5° to + 6° 

0- 960 

1- 4630 

about + 70° 

By reduction fenchone is converted into fenchyl alcohol, melting 
at 45°. Fenclijd alcohol always has an optical rotation opposite 
to that of the fenchone from winch it is prepared. 

FENCHYL ALCOHOL. — ^The chemistry of fenchyl alcohol 
is still in a very unsettled condition, on account of the very similar 
characters possessed by bodies which are probably isomeric and 
difficult to separate in a state of purity. The naturally occurring 
body known as fenchyl alcohol has only been found in the essential 
oil from the root wood of Pinus paluslris. Two artificial fenchyl 
alcohols have been prepared by Schimmel & Co. {Beport, October, 
1898, 49 ; April, 1900, 55, 60) which are described as fenchyl alcohol 
and isofenchyl alcohol. They have the following characters : — 

renchyl alcohol. Isofenchyl alcohol. 
Melting point ... 45° . . 61° to 62° 

Boiling point . . . 92° at 11 mm. .. 98° at 13 mm. 

, Boiling point of acetic ester . 88° at 10 mm. . . 99° at 14 mm. 



FENNEL OIL. — ^This oil is the product of the distillation 
of the fruit of Fcemcxilum vulgax'e, an umhelliferous plant grown 
in various parts of Europe, not only for its fruits, but also for its 
edible root. It is found in most parts of Europe, being especially 
common on the Mediterranean littoral, in Germany, . Moravia, 
Galicia, Bukovina, Moldavia, Boumania, France, Italy, and 
Macedonia. It is also found freely in Persia, India, and Japan. 
Two special types of oils are recognised in commerce, known as 
“ sweet ” and “ bitter ” fennel. The sweet fennel oil is the 
product of the plant frequently known as Fo&nioulum dulce, 
which is, in all probability, only a variety of the ordinary wild 
plant. It is also known as Homan fennel. The ordinary wild 
bitter fennel, growing chiefly in France, Spain, Algeria, and 
Japan, yields the so-called bitter fennel oil. 

The yield of ordinary or cidtivated bitter fennel oil depends on 
the district from wliich the fruits are collected, varying from 
3 to 5*5 per cent. According to Schimmel & Co., the principal 
commercial varieties yield the follovdng amounts of essential 

on : — 

Per cent. 

Saxon fennel (Liitzen) . . . 4:-4-5‘5 

Galician . . . . . 4-6 

Moravian ..... 3 

Roumanian . . . . . . 4’6 

The distillation residues are of great value as fodder for cattle. 
When dried, they contam from 14 to 22 per cent, of proteids, and 
12 to IS- 5 per cent, of fat. Normal bitter ferniel oil has the follow- 
ing characters : — 

Specific gravity . . . 0-965-0-977 

Optical rotation . . -j- 11° to -f- 24° 

Refractive index . . l-5280-l*53S0 

A good quality oil congeals vdthin the limits -|-'5° to -f- 10°. 
The oil is soluble in its own volume of 90 per cent, alcohol. 

The principal constituent of the oil is anethol, which accounts 
for its odour resembling aniseed oil. It is present to the extent of 
50 to 60 per cent, in high grade oils. It is also contains fenchone 
{q.v.), which is absent from the so-called sweet fennel oil. The 
terpenes pinene, camphene, phellandrene and dipentene are also 
present, as well as small quantities of methyl-chavicol, anisic 
aldehj^de, and anisic acid. 

The oil obtained from the sweet or Roman fennel, which is 
obtained to the extent of from 2 to 3 per cent, from the seed 



gro-mi in Southern France, has a high anethol content, and is free 
from fenehone. It has a specific gravity 0-976 to 0-980 ; optical 
rotation -— 5 ° to + 1G° 30' ; and congealing point -4-10° to 

I\Ineedonian fennel oil resembles the French sweet fennel oil. 
It has a sweetish taste, due to its high anethol content and its 
freedom from fenehone. The yield is from 1-7 to 2-8 per cent. 
The oil has a specific gravity 0-970 to 0-980 ; optical rotation 
-f 5° to 4-12° ; and congealing point -f- 7° to -f- 12°. Sicilian 
fennel oil is distilled -from Fcc7iiGiduni pijici'itian, Icnomi in Sicily 
as ass's fennel {Finocchio d’ asino). The fruits are used as a spice 
in southern Italy. Thej’’ jneld about 3 per cent, of essential oil, 
of specific gravity about 0-950, containing little or no anethol, 
as it does not congeal even at — 5°. 

The wild growing plants of the bitter fennel, found in France, 
Spain and Algiers, jdeld about 4 per cent, of essential oil of 
specific gravity 0-905 to 0-925, and optical rotation -j- 40° to 
4- 68°. The principal constituent of this wild oil is the terpene 
cZc.'ciro-a-pheUandrene. It also probabty contains the compound 
di-para-methoxy-stilbene, melting at 214° to 215°. 

The Japanese oil is distilled from very small fruits, which 
are knovm as J apanese aniseed. The 'oil very closely resembles the 
ordinary German oil. 

Tard}’’ (“Etude analytique sur quelques essences du genre 
anisique,” These, Paris, 1902, p. 23) has examined the oil from 
Algerian bitter fennel. It had a specific gravity 0-991 ; and 
optical rotation, -f 62°. In it were identified pinene, phellandrene, 
fenehone, methyl-chavicol, anethol, a sesquiterpene, and, probably, 

The herb yields an oil which differs from that of the fruits, but 
'this oil has not been fullj’- examined. The oil distilled, however, 
from the herb Fcsniciihm capillacezim in Java (from the leaves 
and stems) was fmmd {Jaarh. dep. Land. Ned. Ind. Batavia, 1907, 
45) to have a specific gravity 0-970 ; optical rotation, 4- 40°50' ; 
and congealing point, 12-8°. Anethol and methyl-chavicol are 
present in the oil. 

The fruits of the water fennel Oenanthe Pliellandrium yield 
from 1 to 2-5 per cent, of essential oil. This has a powerful and 
penetrating odour, and has the following characteristics : specific 
gravity, 0-850 to 0-890 ; optical rotation, -f 12° to 4-19° ; refrac- 
tive index, 1-4840 to 1-4950. It consists very largely of the 
terpene phellandrene. It also contains an aldehyde 0^ H^gO 



which has been named phellandral ; an alcohol Ojq H 20 0, termed 
androlj and an alcohol of unknown constitution. 

Sage and Goodale (P. c& E. 0. R., 1922, 18) have examined a 
Spanish fennel oh, the yield being 3*75 per cent. 

The oil has a sweet taste and good flavour, and possesses the 

following characters : — 

Speciflc gravity at 16'5° . . . 0-9638 

SiDecific gravity at 25-0° . . . 0-9571 

Refractive index at 25-0° . . . 1-5243 

Optical rotation at 20-0° . . . + 17-8° 

Solubflity in 80 per cent, alcohol . 1 in 5 

Congealing point . . . . — 3-5° 

By fractionally distiUing the oil, under ordinary atmospheric 
pressure, they obtained the following yields : — 

3?cr CGiit* 

Distniing between 180° and 200 ° . . 7 * 

., 202° „ 210° . . 18 

„ „ 210° 225° . . 57 

,, ,, 225° ,, 235° . . .15 

above 235° ... 3 

The low congealing point of the entire oil shows that it contams 
a low proportion of anethol, but the fraction distilling between 
225° and 235° was found to have a congealing point of 13-3°, and 
the separated solid was undoubtedly anethol. 

They attempted the oximation of the oil and of the low^er 
boiling fractions, but found practically no ketone present, and 
the yields being under 2 per cent, indicate the absence of notable 
proportions of fenchone. The oil yielded reactions indicating 
the presence of some pheUandrene, but the proportion must have 
been quite low. 

It is apparent from these experiments that these fruits, as 
grown in Spain, do not yield an oil containmg anj’- notable pro- 
portion of fenchone, and that the amornit of anethol cannot be 
considered sufficiently high to make the oil as good for. medicinal 
purposes as oil from Saxon or Galician feimel. 

FERULA SUMBUL, OIL OF.— See “ Sumbul Oil.” 

FEVERFEW OIL. — ^The oil of Pyretlimm farthenium is 
distilled on a small scale. It contains a terpene, borneol, and 
bornyl esters. Its specific gravity is from 0-900 to 0-960. 

fixatives. — ^T he question of the lasting power of perfumes 
is one which is of the highest importance to the perfumer to-day, 
as the general tendency has grown to requiring perfumes which 



shall be lasting and tenacious, a s differentiated from t hose which, 
h owcTcr sweet, votatilise very rapid ly. To-day it is necessary 
to recogniso'tTiat tliere are two ver^harply differentiated classes 
of fixatives. There are, in the first place, those which are so 
nearl}- odourless, either se or on account of the minute 
quantities necessary in jwactice, and so act almost entii-ely as 
j)ure fixatives only : and, in the second place, there are those 
powerful fixatives which are also highlj' o doro us themselves, so 
that they modify the odour of the other~ consl^uents of the 
perfume to a more or less noticeable extent, and to that extent 
become active odom* bearers in the perfume itself, as well as mere 
fixatives. At one end of this series there are, of course, those 
whose contribution to the odour is but slight, and again, at the 
other end of the series, those that definitpl}’’ contribute to the 
odour in such a way that, as the more Volatile constituents 
evaporate, the odour of the ” fixative ” becomes more pronounced. 

It has been said that the ideal fixative is one which will equalise 
the differing rates of evaporation of the various odorous con- 
stituents of the perfume. This, however, is scientifically quite 
inacciu:ate, as the alteration in the vapour tension of one liquid, 
when mixed with another liquid of different vapour tension, is a 
mathematical matter depending on the individual liquids them- 
selves. 3?or example, if bergamot oil, neroli oil, and lavender oil in 
an eau de Cologne would (to put it in popular form) evaporate in 
A, B and C hours respectively, the addition of a given fixative will 
cause the evaporation periods to become A -f- X, B -f- X^, and 
C -b X2 respectively, where X, X^ and X^ may be different, and 
in general A -f.X, B -f- X^, and C -b X^ wiU almost certainly be 
different. The real effect ^vill have been a general prolongation 
of the whole of the perfume, which mil, during the evaporation 
period, gradually change in nature according to the loss of any 
given constituent. The gradual development of the public taste 
in favour of tenacious perfumes has led to the manufacture of 
numerous artificial fixatives, and to-day it is correct to say that 
hardly any perfume formula can be considered complete mthout 
its ipcluding a recognised fix ative. Fixatives may broadly be 
classified as follows : — 

(1) Pure fixatives, which do little else than render the perfume 
-less fugitive. 

(2) Fixatives having a pleasant odour, which modify the 
perfume itself in a noticeable (more or less) degree. 

(3) Fixatives having a disagreeable odour, which are used in 



minute quantity and Avliicli, in the very dilute solution in which 
they are used, heconie insensibly agreeable, like “ garlic smeared 
round the salad bowl.” 

Deodorisation of alcohol is, of course, a misnomer in regard to 
-fixation. The use of any ordinary fixative on an alcohol wliich 
has an undesuable odour merely acts as a cover, and does not in 
any way destroy the bad odour. In fact, it is no exaggeration to 
say that more rubbish has been VTitten in regard to the question 
of fixatives than in most branches of practical perfumer}^'. No 
fixative wiU “ overcome ” the effects of S 3 mthetics. The truth i^s 
that these “ effects ” do not require overcomi ng. If the perfumer 
wants a perfume of overpowering strength, as certain classes 
demand, he vdtl use an excess of synthetic s and get his powerful 
odour . If he does not want this, he vdll use minute quantities 
of S 5 Tithetics which do not, when properly used, produce any 
result which requires the words “ harsh ” or “ chemical ” to' 
describe it. Fixatives do not enter into this question at aU. 

The classes of fixatives given above are recruited from three 
main sources : (1) animal substances ; (2) vegetable oils, resins 
and balsams ; (3) artificial or synthetic compounds. 

Fixatives derived from animal sources have long been held in 
high esteem by perfumers. The bodies employed for this pm-pose 
are musk, ambergris, civet, and castor . It has been seriously 
suggested that the popular use of these animal perfumes was 
initial^ due to what the French have named ‘ Vodeur de chair' 
and that the animal perfume had a sex attraction. This suggestion 
vdll hardly bear examination. There is no doubt that the four 
main animal fixatives do fix the perfume exceeding^ well and, 
when used vith discretion, do not interfere with the main floral 
odour when such is being used. For example, the highly disagree- 
able civet, wliich in the natural state has a foul faecal odour, is 
used in the finest wliite rose perfumes manufactured, and at no 
stage of the evaporation of the perfume does any disagreeable 
civet odour become apparent. 

The principal natural vegetable fixatives are the balsams, gum - 
resi ns, and veiy high-boiling essential oils whose constituents are, 
very frequentty, sesquiterpenes and sesquiterpene alcohols. 
Amongst artificial substances used as fixatives there are a number 
which are practicallj’’ only fixatives, although they may be used 
as solvents as well, for example, benzyl benzoa te, with its high 
boiling point and its useful solvent action on artiBcial musk ; 
and there are a* number which have very marked odours as well 



as fixative properties. Por example( ^diphenyl oxide ^ sometimes 
referred to as a fixative. In fact, it Is a high-boiling substance 
'svith a powerful geranium odour, and is more correctly described 
as an artificial geranium perfume of great las ting power. For an 
exhaustive list of substances classed as fixatives, but which 
^ should be examined carcfuUy in regard to the real proportion 
between odour value, reference may be made to the following 
works : Durvelle, “ The Preparation of Perfumes and Cosmetics ” 

I (London : Scott, Greenwood & Co.), 1923, pp. 124r-126 ; and 
Poucher, “ Perfumes and Cosmetics ” (London : Chapman and 
Hall), 1923, pp. 201-203. 

FLEABANE OIL. — ^The fresh flowering herb Erigeron cana- 
densis jdelds about 0-5 per cent, of an aromatic essential oil known 
as fleabane oil. It contains limonene, terpineol, and traces of 
citronellal, and has a specific gravity 0-855 to 0-870 ; optical 
rotation, -f- 52° to -}- 81° ; acid value, 0-15 ; and ester value, 34 
to 109. 

FLORIDA WATER. — ^This perfume, which, of course, is not 
protected with a proprietary name, is one of exceedingly popular 
character in America, and, to a smaller extent, in far Eastern 
countries that import it. It is, in the United States, largely what 
lavender water is in England. It is a toilet perfume somewhat 
resembling a mixture of lavender water and eau de Cologne, 
rounded off with one or more of the following bodies ; cassia oil 
(or cinnamon oil, or cinnamic aldehyde) ; elove oil (or pimento 
oil, bay oil, or eugenol) ; and lemongrass oil. 

FOIN-COUPE. — ^This popular type of perfume is supposed 
to reproduce the odour of new-mown hay. It is invariably based 
on coumarin, modified by lavender, bergamot, and other perfumes, 
according to the exact note the perfumer wishes to give to his 
product. The odour of true new-mown hay is due more to the 
sweet-scented grass known as Anihoxantlmm odoraium than to 
any other grass, although many others contribute to it. Several 
different types of clover, of course, also add to the fragrance of the 
hayfield odour. This odour is probably the result of glucosidal 
decomposition of constituents present in the plants, resulting in 
the formation of a little coumarin. (See Anxctican Perfttmer, 1922, 

FORMYLATION. — See “Alcohols, Determination of.” 






FRAGAROL.— See “ ^-Naplitliol-butyl Ether.” 

FRANGIPANI.— (See also “ Plumiera.” )— This name is 
applied to a particular tj^pe of fancy perfume which, at one time, 
achieved great popularit}'' in this country. The name is said to 
have been derived from the office held by an old Roman family, 
namely, of breaking the bread (the meaning of the word) in the 
celebration of holy communion. A descendant of this family, 
which appears to have adopted the official title into its name, 
is said to have introduced a special perfume for gloves wdiich is, 
at least by legend, the lineal ancestor of the modern “ Frangi- 
pani ” (see below). The name was, at all events, given by 
French colonists in the West Indies to the odorous plants Phimiera 
nibra and Plumiera alba. These trees belong to the natural order 
Apocynaceoi. They are natives of Peru and other parts of South 
America, and are found in several of the West Indian islands. 
The genus was named bj’^ Tommefort in honom’ of Charles Plumier, 
a Franciscan traveller in South America and author of several 
works on botany. Phimiera rubra is called b}^ the French in the 
West Indies Frangipanie rouge, and also “ red jasmin.” It is a 
tree from 12 to 20 feet in height, yielding highty odorous flowers, 
which are used b}^ the native women to perfume their linen as 
we use lavender flowers. Several other varieties are cultivated, 
and are highl}^ odorous. Amongst them is Phimiera acutifolia, a 
plant which is cultivated in cemeteries in the Philippine Islands. 
The flowers have a marked “ frangipani ” odour, but no essential 
oil has been obtained from them. Racon [Philip. Jour. Science, 
1909, 4, A, 131) showed that if the flowers be heated to 40° the 
odour was destro 3 ’'ed. An extract was obtained by' means of 
petroleum ether with the t 5 ''pical odour of frangipani, although 
no essential oil could be obtamed. 

But the flowers of Phimiera aciiiifolia exhale a very pleasant 
and highly esteemed perfume. Descourtilz, in his “ Flora of the 
Antilles,” praises with voluble enthusiasm this “ sweet odour,” 
comparable, he saj^s, with that of the tuberose or gardenia, and 

much in demand by the young girls on fete-days.” The creoles 
place the freshly gathered flowers of the frangipani in their 
linen and in them rooms, and the planters, to honom’ them guests, 
often strew the beds with these blossoms. This very penetrating 
perfume still persists for a fairly long time after the flower has 
been separated from the tree on which it grew. It was doubtless 
in imitation of this that boquets a la frangipane were formerly 



Thi=; species cultivated in India, but its origin is Centi-al 
America, probably somewhere about [Mexico. It is not indige- 
nous in tropical Asia, as A. de Candolle believed. In India the 
flowers are laid in the temples and on the graves, as offerings, 
Li the Philippines, t\\o Plumiera is frequently used as a “ cemetery 
tree " ; they plant slips which take root easih' and grow rapidly. 

The following interesting account of this perfume is due to 
Daniel Hanbury and was written in 1S.50, and is abstracted in the 
Pcrpnncrij avd Esscntlnl Oil Record (1915, 238) as follows : — 

Frangipani is the name of a ver}' ancient, aristocratic Roman 
famil}' dating from the eleventh centuiy, a member of which, 
Ceucio Frangipani, became a leader of the Ghibcline faction against 
the Guelphs during the century following, and man}- times since 
then has the family figured in the romantic histor 3 "of Italjx On 
board the Santa 3Iaria with Columbus was one Jlercutio Frangi- 
pani, and in the Papal army assisting the French King Charles IX. 
against the Huguenots was a Mutio Frangipani. The grandson of 
the latter was the IMarquis Frangipani, iffarechal des Armees of 
Louis XIII., and he it was who turned his ingenuity to a very 
unmilitary invention, a method of perfuming gloves, which when 
so scented Averc known as ” Frangipani gloves.’’ The authority 
is Menage, in liLs ” Origini della Lingua Italiana,” published ait 
Geneva in 1GS5 ; he saj^s “ Da uno di que Signori Frangipani 
(rabbiani veduto qui in Parigi) fiirono chiamati certi guanti 
profumati, Guanti di Frangq^ni ” [from one of which Frangipani 
(I saAv him here in Paris) Avere named certain perfumed gloves, 
“ Frangipani gloves ”J. From another old record, Le Laboureur's 
“ ]\Iemoh-es de Castelnau,” wo learn that a brother of the Marquis 
was also associated with the invention : “ Ce dernier JIarquis 
Frangipani, et son frere mort auparavant lu 3 ’-, inventcrent la 
composition du parfura et des odeurs qui retiennent encore Ic nom 
de Frangipane.” 

In an extraordinary AA'ork entitled “ Frangipani’s Ring : an 
Event in the Life of Henry Thode,” translated from the German 
and published in London by Jolm Macqueen in 1904, reference is 
made to a AA'ork entitled “ Chronicle of the Island of Veglia and 
of the Frangipani Family upon this Island,” by Antonio Vinci- 
guerra, Secretar 3 ’- of the Senate and the Republic of Venice, a 
Avork mentioned in the Catalogue of Manuscripts in St. Llark’s 
Library in Venice. Thode, attempting to trace the origin of the 
family, Avrites of it as follows : — - 

“ A stalwart race, inliabiting strong castles in Croatia, Avith its 




ancestral seat in Modi-usa and Segna (Zengg), which was given 
it in fief hy Bela III. in 1260. Driven about by their passions 
througli the following centuries to ambitious scheming, wild 
undertaldngs, and outrageously violent deeds ; forced by their 
tcrrifyuig superstitions to take refuge in fantastic religious 
devotions ; heroic and faithless, um’uly and calculating in capricious 
change, thej’- wasted their turbulent lives in warring with their 
neighbom’S and with themselves. 

“ Whence the race original^ came cannot now, with any 
certainty, be stated. One authority contends that its home from 
the first was in Croatia, and that the name, literally ‘ Frankopan,’ 
means ‘ Francis the Lord ’ ; others assert that it was a severed 
branch of the Roman famity of the Frangipani, whose annals 
are stained "with the dastardly betrayal of the last Konradin of 
Hohenstaufen bj'' the Lord of Asturia, John Frangipani, and 
vith the treacherous assassination of Duke Frederick the Warrior. 
Contrary to tliis, the authors of the Venetian genealogies, and 
among them the earliest, so far as I Icnow, Francesco Venier and 
Zancarola, relate in their chronicle (now in St.’ hlark’s Library) 
that in former times a family of the Frangipani came from 
Ravenna to Venice, where they became members of the Great 
Council, and that, with the death of Giovanni, who held a position 
in the hlint, this line became extinct in 1347 ; they also hold 
that from these Ravenese-Venetian Frangipanis the Croatian 
braneh originally sprang.” 

It vdU be noted that the Italian writers mention only per- 
fumed gloves, whereas La Laboureur speaks of “la composition 
du parfum et des odeurs,” which would appear to include some 
essence, powder or pomade. This much is certain, however, that 
certain compositions as ^mnade, essence and powder, styled 
Frangipani or Frangiptane, were sold by perfumers dorni to a 
century ago, when they appear to have fallen into disuse. A 
revival of certain peilumes bearing the name occurred in the 
’fifties, and formulas apj)eared in Piesse’s “ Art of Perfumeiy,” 
London, 1S56, and Celnart’s “ Nouveau Manuel Complet du 
Parfumeur,” Paris, 1854. The various formulas to be found vary 
so much among themselves that, obvionslj’’, they camiot all 
represent the original. “ Pharmaceutical Formulas ” (MacEwan, 
1914) gives tlnee such recipes from which to choose, and judging 
from their constituents one might describe them as dainty, rich, 
and heavy respectivety, according to the predominance of floral 
extracts, otto of rose, sandalwood, civet, ambergris, and musk. 



It may be taken for granted that the basic odour of *• frangi- 
pani ■’ perfumes to-day is that of jasmin, modified with substances 
having hea.vy odours.’’ 

FRANKINCENSE.— Sec “ Boswellia Resin.” 

FUMIGATING PASTILLES.— Fumigating pastiUes are 
usuaiiv moulded into the shape of cones, and are prepared from 
pastes from which the water is driven off after the pastilles have 
been cut into shape bj* approju’iate moiilds. These pastes are 
made up from selected varieties of charcoal, with potassium 
nitrate to ensure even and continuous burning, and mixed aromatic 
gums and balsams, Avith other aromatic volatile substances to ghm 
a highly aromatic odour on buming. They are. in fact, little else 
than “ moulded incense.’’ Frecpicntly a little powdered cas- 
carilla bark or other substance burning with an aromatic odour, 
is added. Benzoin and storax are the usual balsamic substances 
employed, and powdered cascarilla, cinnamon, cloves, cedar 
wood and vetivert root are the usual vegetable poAA'ders used. 
'V^anillin, heliotropin, and the oils of cedarAvood and sandahvood 
are the usual perfume additives. Charcoal is usualty present to 
the extent of 25 to 50 per cent., and potassium nitrate from 
5 to 7'5 per cent. Occasionallj’^ the charcoal is replaced b}’' red 
sandalAA'ood, the pastilles being red instead of black in colour ; 
or by fine white pine saAvdust, Avhen the pastilles are nearly Avliite. 
The exact formula} for the finest odours are, of course, trade 

FUSANUS SPICATUS, OIL OF.— The so-caUed Western 
Australian sandalwood oil is the distillate of the Avood of Ftisanus 
spicatus, a tree originally knoAAm as Santalum cygnonim. The 
oil resembles true sandahvood oil in odour, and contains similar, 
but not identical, constituents. It is of very great value to the 
perfumer, and is largely employed for perfuming soap. The 
natural oil has the folloAAing characters : — 

Specific graAdty . . . 0-957 to 0-972 

Optical rotation . . . 1° to — 8° 

Refractive index . . . 1-5015 to 1-5100 

Total alcohols (as CigHo^O) . 65 to 78 per cent. 

The oil is, however, fractionated so as to contain up to 95 per- 
cent. of alcohols, and is obtainable in this condition on the 

It has recently been fully investigated by Sanjiva Rao and 
Sudborough {Journal of the Indian Institute of Science, vol.'v., xii., 



1923, 163). Tliese authorities give the following account of the 
tree, its wood, and the essential oil : — 

The sandalwood, although only a tree or shrub, is an important 
factor in the timber industry of Western Australia. The species 
is somewhat peculiar in its appearance, and certainly has more of 
the character of a largo bush than of a tree proper. It has alow, 
depressed habit, and is consequent^ decidedly" branchy and 
heavily topped. It is seldom more than 8 inches in diameter and 
12 to 18 feet high, with stems 8 to 10 feet long. 

The value of the wood exported from Australia is given as 
£96,050 in 1882, when the price was £10 per ton, and £117,072 in 
1918-19, when the price of v/ood was £13 per ton. Most of the 
wood finds its way to China and, to a small extent, to other Eastern 
countries. Within recent 3 ’-ears increasing quantities of wood have 
been imioorted into India as shown b}’’ the following figures : — 

Tear. . . . 19M-15 1916-17 1917-18 1918-19 1920-21 

' 10 months 

Value of imported wood .£8,372 £11,080 £16,080 £29,860 £30,370 

The jfield of oil from the w'ood is 2 to 3 per cent, as compared 
with a jdeld of 5 to 6 per cent, for the genuine East Indian sandal- 
wood {Savialmn album). The oil was first distilled in 1875 by 
Messrs. Schimmel & Co., of Leipzig, and subsequent^ the distilla- 
tion was undertaken in Fremantle. [And also near Albanj^, -where 
a distillery existed in 1900. (E. J. P.).] In 1918-19 3,720 lb. of 
oil were distilled in Austraha, and found a market in Australia 
and Java as a substitute for East Indian sandalwood oil in both 
perfumery and medicine. 

The following are the values obtained on the anatysis of fom’ 
samples of the natural oil : — 




Specific gravity at 15/15° 







Refractive index at 25° . 





Optical rotation at 25° . 
Solubility in six parts of 70 per 

— 7-7° 

— 0-7° 

— 0-25° 

— 0-87° 

cent, (by volume) alcohol at 
20° , 





Total alcohols calculated as 

santalol, CigHo 40 

Esters calculated as santalyl 










Acid value . 





PERFU 2t E R r 

A sample of oil B was distilled under atmospheric pressure, and 
throe fractions collected and examined ; the following values were 
obtained : — 

No. of 

roiling point. 

Weiglii in 



O-D i 


Optical rota- 
tion at 25°. 







1-4994 j 


t - 2-0 






, - 






+ 1-2 

During the distillation, fumes and an emp 5 Teumatic odour were 
observed, indicating partial decomposition. 

Two hundred grams of the original oil were saponified with 
alcohohc potash, washed, dried with anhydrous potassium 
carbonate, and subjected to fractional distillation under a pressure 
of 9 to 10 mm., using a pear-shaped fractionating column ■with 
five pears. 

From 180 grams of saponified oil, seventeen fractions and a 
residue were obtained, and the analytical data for these fractions 
were as follows : — 

No, of ! 
. ! 


Pressure : 
in mm. 

Temp, in 






Optical i 
at 25°. j 



index at 

Soluble in 

C vol‘3. of 

70 per cent. | 







- 1 




— 4-8 







— 4-6 







— 4-2 



4 i 




— 3-6 







— 3-5 



6 i 








f 1 




. -1-6 


Clear at 60° 






— 1-3 


„ 45° 


• 9 




— 1-1 


» 35° 






— 1-0 


„ 26° 






— 0-9 


„ 20° 








.. 14° 


- 13 






„ 13° 






+ 0-3 


„ 6° 






+ 1-5 


„ 2° 






+ 1-6 


» 3° 






+ 1-4 


- 28° 









It was found that the oil contained two isonieric sesquiterpene 
alcohols, to which the name fusanol has been applied. The 
characters of these alcohols are here compared with those of the 
isomeric santalols from true sandalwood oil : — 


1 j3-Fusanol, 

! talol. 




Boiling point at 6 mm. . 














. . 






+ 5-7° 

+ 2-6° 

+ 1-1° 1 

— 42° 

Molcular weight found . 



• 215 


Molecular refraction 
Temperature at which mixture 
of 6 '5 parts by volume of 60 






..... 1 


per cent, (by weight) alcohol 
and one part by volume of 
oil becomes clear 

. 5-6° 





12° ; 


The results of this important investigation are summarised as 
foUows : — 

( 1 ) The so-called West Australian sandalwood oil is derived 
from a species of tree quite different from the Sanialum album, 
Linn., the species from which the East Indian oil is obtained. It 
differs in general properties from the East Indian oil and, in order 
to avoid confusion, it should be given a name other than sandal- 
wood oil. 

( 2 ) The oil, as distilled direct from the wood, differs in most of 
its .analytical data from the genuine sandalwood oil. It does not 
fall within the limits allowed by the British Pharmacopoeia as 
regards specific gravity, optical rotation, alcohol content, or 
solubility in 70 per cent, (by volume) alcohol at 20°. 

( 3 ) By fractional distillation and removal of the lower boilmg 
sesquiterpene fraction it is possible to obtain an oil which passes 
the B.P. tests for genuine sandalwood oil, vdth the exception of 
the optical rotation, which is always well below the standard, 
required by the B.P. 

(4) Although it is easy by fractional distillation to obtain an 
oil containing more than 90 per cent, of alcohols (calculated as 
C 15 II 24 O), nevertheless the alcohols present are not identical with 



either of the two santalols present in East Indian oil, but are 
isomeric "with them. 

(5) There appear to be at least two alcohols present in the 
West Australian oil. They are probably to be represented as 
C15H25O, and, in order to distinguish them from the isomeric 
santalols, they have been termed a- and /S-fusanols. 

(G) These fusanols jdeld hydrogen phthalatcs and phenyl- 
urethanes. The fact that they react much more slowh' than the 
santalols with phthalie anhydride indicates that they are probably 
secondary, and not primary, alcohols. 

(7) From their molecular refractions it is probable that both 
fusanols are bicyclic compounds containing two olefine linkings. 

(8) The statement that during distillation of the oil under 
reduced pressure there is a loss of alcohols has not been confirmed ; 
neither steam distillation nor distillation under reduced pressure 
appears to change the alcohol content. 

(9) It is generally agreed that for perfumery purposes the West 
Australian oil is inferior to genuine sandalwood oil. 

The witer (E. J. P.) does not agree vuth conclusion No. 3. 
Fractionation usually results in oils with a specific gravity below 
that of the true sandalwood oil, but the correct optical rotation 
can be attained. 

GALANGAL OIL.— Galangal oil is used as a flavouring 
material rather than as a perfume. It is obtained by the distilla- 
tion of the rliizome of Alpinia officinarum, a plant cultivated in 
Cliina and Siam. The oil has a specific gravity 0-910 to 0-928, 
optical rotation, — 1° to — 8° ; and refractive index from 1-4760 
to 1-4850. It contains terpenes, cineol, and oxygenated con- 
stituents not yet identified. 

GALBANUM. — ^This body is a gum-resin obtained from 
several species of Pcucedaivum, principally Peucedaimm galhani- 
fiormn, belonging to the natural order Umbclliferce. It contains 
from 8 to 10 per cent., sometimes as much as 24 per cent., of 
essential oil of sharp aromatic odour. It is used to a small extent 
as an odorous fixative. The essential oil has the following 
characters : — 

Specific gravity . . . 0-905-0-955 

' Optical rotation . . . — 10° to -}- 20° 

Refractive index . . . 1-4840-1-4960 

It contains pinene, myreene, a sesquiterpene (cadinene ?), and 



a sesquiterpene alcohol, CigHocO, which has been termed cadinol. 
Five samples of the gum resin itself examined by Beckirrts and 
Bruche had the following characters : — 

Specific gravity 






Ash, per cent. 






Resm, per cent. 



; 68 



Acid value of resin 



i 40 



Ester value of resin . 






GARDENIA. — ^Thc gardenia is a highly odorous flower, several 
species of which are cultivated, and whose perfume is highly 
esteemed. The perfume is rarely extracted from the flower, 
most of the boquets knovm by the name being entflely artificial 
productions. The most common of the plants cultivated is 
Gardenia fiorida, also knovm as Cape jessamine ; Gardenia grandi- 
flora is another well-knoum plant. They belong to the natural 
order Biibiacece. The plants are indigenous to tropical Asia and 
Africa, and also the Cape of Good Hope. In Bengal the plant is 
knovm as Gumdlmraja : and in China, where its flowers are used 
for the perfuming of tea, it is called Pah-seyna-lma. The flowers 
from mixed cultivated species jneld, on maceration vdth hydro- 
carbon oil and distillation of the extract, 0-0704 per cent, of an " 
essential oil of specific gravity 1-009, and optical rotation 1-47°. 
At 760 mm. pressure it commences to distil at 204° vdth partial 
decomposition. According to Barone {Boll. Glihn. Farm., 1902, 
41, 489), it contains benzyl acetate, the acetic ester of methyl- 
phenyl-carbinol, linalyl acetate, methyl anthranilate, and 

The artificial perfume is built up on this composition, vith the 
addition of various other synthetics, such as benzyl acetate, 
phenyl-ethyl aldehyde, and geraniol and its esters. (See also 
“ Phenyl-ethyl Alcohol ” and " Gardeniol.”) 

GARDENIOL. — ^This is a fancy name given to the acetic 
ester of phenyl-methyl carbinol, an isomer of iflienjd-ethyl 
alcohol. (See “ Plienyl-ethjd Alcohol ” and “ Gardenia.”) 

GAULTHERIA OIL. — See “ Bhch (Sweet), Ofl. of.” 

GENET. — See under ” Broom.” - 

GERAN ALDEHYDE. — ^This is an alternative name for the 
aldehyde citral CjoHieO [g.v.). 



GERANIOL. — Geraniol is one of the very important sub- 
stances in the perfume industiy. It is found in numerous essential 
oilS; both in the form of esters, of which the principal is geranyl 
acetate {q.v.), and in the free state. For example, palmarosa oil 
contains SO per cent, or more of free geraniol ; citronella oil 
contains a considerable amount j all forms of geranium oil 
contain much geraniol in the form of esters, and a certain amount 
in the free state ; and it is an important constituent of otto of 

Geraniol is not manufactured synthetically, hut is extracted 
without anj^ great trouble from oils wliich are rich in it, so that 
it is a regular commercial article, and is used to a large extent in 
the compounding of artificial perfumes. 

Geraniol is a colourless, sweet smelhng oil, having a rose-hke 
odour. Its formula is CioHi^OH, so that it is isomeric with 
nerol and with linalol. Its characters are as follows : — 

Specific gravity . . . 0-880-0-883 

Optical rotation ... 0° 

Refractive index . . . 1-4766-1-4786 

Boiling point. . . . 228°-230° 

It can be separated from those oils which contain an appreciable 
amount of it, by first concentrating it in the appropriate fraction 
uiider reduced pressure, and then mixing the fraction intimately 
with an equal weight of absolutely dry powdered calcium chloride, 
and allowing the mixture to stand in a desiccator for sixteen 
hours at a temperature, of about — 5°. The pasty mass is then 
rubbed down with dry petroleum ether, and the liquid portion 
removed from the solid portion by means of a suction filter. 
After washing with more petroleum ether, the solid compound of 
geraniol vdth calcium chloride is treated with water, which 
decomposes the compound, with the hberation of the geraniol, 
and the oil is purified by fractional distillation. The geraniol 
distfis over at 228° to 230°. To prepare it in a state of absolute 
purity it should be treated with sodium, and then dry ether and 
phthalic anhydride added. The geraniol sodium phthalate is 
hydrolysed by alcoholic solution of caustic potash, and the pure 
geraniol precipitated by the addition of water. 

Rlatau and Labbe effect the separation of geraniol and 
citronellol, which often occur together, in the foUovdng manner. 
The oil, first' saponified, in order to decompose esters present, is 
fractionally distilled in vacuo. The fraction distilling at 120° to 
140° at 30 mm. pressure, is heated with its own weight of phthalic 



anhydride and its own volume of benzene. The niixture is 
dissolved in a solution of sodium carbonate, the solution extracted 
with ether, and the acid phthalic esters of geraniol and citronellol 
liberated by the addition of hydrochloric acid. These esters are 
dissolved in petroleum ether, and the solution cooled to — 6°. 
Under these conditions, the acid ester of geraniol separates out 
in the crj^stalline condition, whilst that of citronellol remains in 
solution. The esters, on saponification, yield the corresponding 
alcohols in a state of comparative purity. The geraniol ester 
melts at about 47°, and forms a silver salt which melts at about 

Geraniol is characterised by its yielding a compound with 
calcium cliloride, as above described, and by the formation of a 
phenylurethane melting at 82°. On oxidation geraniol is con- 
verted into its aldehyde, citral (q.v.). 

Semmler and Schossberger {Berichic, 44, 991) have prepared 
an isomeric geraniol, which they have named isogeraniol. Geraniol 
can be, as just mentioned, oxidised to citral. If citral be heated 
with acetic anlij^dride, an alteration in its constitution takes 
place by the migration of a CHo group. The citral is “ cnoUsedP 
The resulting omZ-citral is reduced by means of sodium amalgam 
and alcohol, when the isomeric alcohol is obtained. Isogeraniol is 
an oil having a pleasant odour of roses, and possesses the following 
characters : — 

Boiling point at 9 mm. . . 102°-103° 

Specific gravity at 20° . . 0'S787 

Befractive index . . . 1-4732 

For the estimation of geraniol, see under “ Alcohols, Deter- 
mination of.” 

The following method for obtaining geraniol commerciall3'' is 
given b}’’ Lewinsohn (P. <9 E. 0. R., 1924, 282) : — 

Java citroneDa oil is worked up cliiefly for its geraniol, but this 
can onty be produced economically if the citronellal obtained 
at the same time is further worked up for d-citronellol. It 
is, moreover, advantageous to separate from the residues the 
sesquiterpene compounds they contain, as thej’- have very 
valuable fixative properties and find application in numerous 

Thirty kilos of Java citronella oil are placed in a copper distilla- 
tion vessel, to which is attached a copper fractionating column 
about 6 cm. in diameter and 120 to 140 cm. high, filled with glass 



bends or, better, \ntli Rascheg rings, the vessel being heated by 
direct gas flame. The exit-tube of the column is connected vdth a 
copper spiral immersed in an iron tank of cold v'ater and leading 
to a large vacuum flask which serves as a receiver. A stop-cock 
between condenser and receiver enables the latter to be changed 
wliile maintaining the vacuum in the distillation vessel. It is 
useful also to modify this arrangement, so that two receivers can 
be employed. 

For the first distillation of the oil a not too liigh vacuum — saj’-, 
about 10 mm. — is most suitable. The “ crude first runnings ” are 
the liquid distilling below 95° at 10 mm., thus ensuring the absence 
in the next fraction of anything boiling below the boiling point of 
citronellal. The second fraction, from 95° to 110°, is called 
“ crude citronellal.” These two fractions must be distilled slowly 
to avoid overheating, but after 111° distillation may take place 
more rapidly, since only httle citronellal will appear in the “ crude 
geraniol ” now collected. The heating is discontinued at 130°, 
and the residue in the distillation vessel is transferred to an 
enamelled container, where the residues from several operations 
are later worked up for sesquiterpene alcohols. 

AU three distillates are now redistilled separatefy, the crude 
first-running ’’ at 10 mm., the other two fractions at 3 mm. 

The first fraction is distilled up to 99° at 10 mm., and the 
residue, consisting mainly of citronellal, is added to the “ crude 

The second fraction is distilled up to 105° at 3 mm., and the 
residue is added to the “ crude geraniol.” 

In this wa 3 ^ are obtained a “ final first-runnings ” (about 5 per 
cent, of the citronella oil used), and 50 to 52 per cent, of “ teclmical 
citronellal,” which contains about 75 per cent, of pure citronellal, 
and is worked up for “ d-citroneUol.” 

By the redistillation of the third fraction (“ crude geraniol ”) 
there is first obtained a little citronellal, which is added 
directfy to the “ technical citronellal.” The main fraction, 
namely, “technical geraniol,” comes over at 115° to 120° at 
3 mm. The residue is added to the contents of the enamelled 

In order to convert “ technical geraniol ” into “ pure geraniol ” 
it is necessarj’^ to remove completely the small traces of citronellal 
which spoil its odour. This is done by boiling for several hours 
with dilute caustic soda, whereby the aldehyde citronellal is 
resinified and remains in the residues on subsequent rectification. 



The operation is best performed in a double-M^allecl iron vessel 
fitted with a good reflux condenser. After boiling for four hours, 
the mixture is diluted with cold water and the npjier oily layer 
is separated from the lower aqueous layer. The oil is washed 
twice V'ith lukev^arni water, then with 50 per cent, acetic acid 
until just acid, next with sodium bicarbonate solution until again 
allcalinc, and flnall}'- once more with Avater. 

The oil is now distilled in vacuo from a 5-litre glass flask in an 
oil bath (or, for larger quantities, from a copper vessel). Time 
geraniol comes over at 115° to 11S° at 3 mm. as a Avater-clear 
liquid. The yield is 95 per cent, of the “ technical geraniol.” 

GERANIUM, OILS OF. — The true geranium oil must not 
be confused AAith the so-called Indian (or Turlcish) geranium oil. 
The latter is actually the East Indian palmarosa oil, an oil dis- 
tilled from a member of the natural order Graminece (see under 
” Gingergrass Oil ”), whilst true geranium oil is the pi'oduct of 
various species of pelargonium belonging to the natural order 
Gcraoiiacece. The principal species distilled arc Pelargonium 
odoraiissimum, P. cajnlatum, P. gravcolcns, and varieties of 
P. Padula, together with, in all probability, numerous hybrid 
forms. According to E. M. Holmes (P. E. 0. P., 1913, 239), 
the majority of the species of pelargonium are nathms of the dry 
rocky slopes of South Africa, but in then’ natural surroundings 
they are someAvhat stunted in groAvth. ^Yhen plantations are 
laid out in the south of Europe or in Algeria, etc., the}’- are 
general!}^ established on low-ljdng ground kept moist by a system 
of irrigation, so that the plants groAA’ luxurious!}’- after attaining 
a height of 2 feet 6 inches to 4 feet, AAith stems nearly an inch in 
diameter. The result is that three crops of leaves can usually be 
distilled annually AA’lien the groAvth is luxurious — as it is, for 
example, in Algeria. This, hoAA’CA’-er, is not the ease in the south 
of France. A considerable proportion of the geranium oil of 
commerce is distilled in the island of Reunio2i, and is knoAvn as 
Bourbon geranium oil ; a large amount is also distilled in Algeria, 
and a certain amount is produced in Spain, Italy and Corsica. 
According to Holmes {loc. cit.) the plant used at Grasse, so far as 
can be judged from the leaf of the plant, appears to be Pelargonium 
capitaium. The plant cultivated in Bourbon is generally stated 
to be the same species, but -the Bourbon-distilled oil more nearly 
corresponds in odour Avith that of the allied species Pelargonium 

In Grasse the plants are propagated by means of cuttmgs, set 



out in October in sheltered beds, protected in frosty -weather by 
means of straw mats. The cuttings are taken from the nurseries 
in April and planted out in open fields, where, under verj- favoim- 
able conditions, they will grow to 4 feet m height. In the 
neighbom’hood of Kice they flower in August, but in cooler 
districts, such as Grasse, in October. The time of cutting in 
Algeria lasts from early spring until mid-autumn. In Bourbon 
the cutting proceeds during nearty the whole year. It has been 
found that the best jdeld of essential oil is obtained after a few 
da 3 's’ rain, and when the leaves are gathered in tlic earlj' morning 
before the buds have opened. The first crop in Bourbon is taken 
in April, the second in June, and the third in October. The 
plants require careful handling, as when the leaves are crushed 
there is always a loss of essential oil. In Reunion, as well as in 
Algeria, every geranium farm of anj'- importance possesses its ovti 
still. In most cases care is taken to emplo^y a form of still with 
a double bottom so that the leaves are not burned. 

According to Cordemoj'- {Rev. cultures coloniules, 1904, 14, 170), 
the species cultivated in Reunion is Pelargonhim capiiatum (but 
see above). The plant flourishes best here at altitudes between 
400 and 1,200 metres, the lugher regions bemg too cold in the 
winter time. There are between 250 and 300 distillers of tlic oil 
in the island. About 700 to 1,000 kg. of geranium leaves are 
necessar}’- to 3 'ield 1 kg. of oil. 

In Corsica an excellent oil is produced on a small scale. Pelar- 
gonium odoratissimurn bemg the principal species used. A few 
modern steam stills have been installed, and if modern methods 
are applied and transport difficulties are overcome (and these 
are very serious in Corsica), there is undoubtedly a big future 
for geranium distillation. As much as 1,300 kg. has been 
distnied in Corsica in a year, but this is considerably above the 

Spain produces from 500 to 1,000 kg. of geranium oil in Valencia 
and Andalusia. 

■ According to Ducellier (“ Le geranium rosat. sa culture en 
Algeria,” 1913, Algeria) there are about 2,200 acres m Algeria 
planted -with geranium. There are plantations at Rovigo, Chelbi, 
BoufarHi:, Borurian, MouzaiaviUe, Morocos, S. Faoueli, and other 
places. According to this authority, only Pelargonhnn graveolens 
is cultivated for distillation, and he considers, on the authority of 
Knutt, that Pelargonium capitatum is a h 3 ’'brid of that plant. 
Whilst the Algerian geranium is propagated b 3 ’- cuttings, it is not 



necessary to renew the plantations every year as is done in the 
south of France, as the Algerian winter is not severe enough to 
kill the plants. In some districts they will live for ten to twelve 
years. In Algeria, as in Spain and Reunion, three crops of leaves 
are gathered annually — one in early spring, a second in June, and 
a third in October. 

The cultivation of the geranium j)lant is of paramount import- 
ance if a good yield of oil is to be obtained. This is especially true 
in the districts less favoured by natural conditions. Boutilly has 
clearly established the fact that superphosphate of lime is very 
favourable to high production of oil, and advises using tliis mamtce 
to the extent of about 800 lb. per acre. One of the most successful 
fertilisers for geranium plants is a mixtm-e of sodium nitrate 
(200 parts), ammonium sulphate (150 parts), superphosphate of 
lime (300 parts), and potassium sulphate (150 parts). (See also 
P. c& E. 0. R., 1913, 381, for cultural details.) 

The leaves are the odom' bearing portion of the plant, the 
flowers being practically odourless. Sometimes the oil is redistilled 
over rose petals, or rose petals are added to the geranium leaves 
when distilled. The resulting oil is, of course, of exquisite odour, 
and is sold as “ oil of rose-geranium.” 

Charabot and Laloue have studied the development of the 
odorous constituents in the geranium. They found that these were 
entirely absent in the petioles and stems, and were only to be found 
in the leaves, where they appear to have their origin. The oil was 
distilled from the green plants in July, and again, from exactly 
similar plants, in August. These two distillates were found to 
have the following characters : — 

Specific gravity 
Optical rotation 
Acid number 

Free alcohols . 
Total alcohols . 


— 10 ° 





per cent. 



— 10° 16' 




per cent, 


It was thus shoAvn that (1) the acidity decreases as the 
plant matures, (2) the oil becomes richer in esters as grovi}h 
proceeds, (3) the amount of total alcohols increases slightly 
and the amount of free alcohols decreases slightly as vegetation 

They also obtained interesting results in the examination of the 
oil separating from, and the oil dissolved in, the distillation waters 



of immature plants. These oils, and the ttvo buUted, had tho 
following characters : — 

Separated oil. 

Soluble oil. 

Total oil. 

Specific pravity 




Optical rotation , 

- 11° 

- 5° 13' 

- 10° 6' 

Acid number 




Ester number . . j 

1 16-6 


1 15 

Saponification number . 



1 57 

Total alcohols 

70 7 per cent. 

77'5 per cent. 

7T8 per cent. 


7*0 per cent. 

2*8 per cent. 

6*3 per cent. ^ 

According to Furukawa {Jour. Chem. Ind. Tohio, 1919, 22, 83), 
experimental cultivation of three species of geranium has been 
carried out on a farm near Tokio. These are Pelargonium gravcolens, 
P. radula, and P. deniiculatum. The oils distilled from the first 
two did not resemble geranium oil of commerce, whereas that 
from P. dcnticulatum resembled commercial geranium oil to some 
extent. The three oils had the following characters : — 

P. gravcolens. 

P. radula. 

P. dcnliculalum. 

Specific cavity . 




Acid number 




Ester number 




Free alcohols 

22-1 per cent. 

17-26 per cent. 

■ 60 per cent. 

Total alcohols 



63-5 per cent. 

Yield of oil 

1-7^2 „ 



Optical rotation . 

+ 4° 6' 

+ 3° 

Puran Singh {Indian Forest Records, v., part viii., 1917, and 
P. & E. 0. R., 1917, 8, 327) has reported upon the wild geranium 
of the Nilgliiris. He states that tliis plant is Pelargonium gravcolens 
{P. terehiniaceum, Harv. and Sond.). A yield of 0-044 per cent, 
of the weight of the entire plant was obtained, the essential oil 
having the follovdng characters : — 

Specific gravity at 16° . 

Optical rotation 
Eefractive index at 18° 

Total geraniol 
Free geraniol 
Esters as geranyl tiglate 
p- 257 

— 5° 39' 

74-8 per cent. 
46-6 „ 




The following values may be taken as covering practically all 
pure geranium oils from the sources named : — 



Specific gravity 

Optical rotation 

Refractive index 

Esters as geranyl tiglate . 
Total alcohols as geraniol . 

- 7° 50' to - 14° 
22-33 per cent. 
67-77 „ 

— 6° 50' to — 12° 
18-30 per cent. 
65-78 „ 



Specific gravity 

Optical rotation 

Refractive index 

Esters as geranyl tiglate . 
Total alcohols as geraniol 

' 0-895-0-905 

— 7° to — 11° 
20-30 per cent. 

0- 896-0-907 

— 7° 20' to — 12° 

1- 4640-1-4675 
26-42 per cent. 


Sicilian (?) 

Specific gravity 

Optical rotation 

Refractive index 

Esters as geranyl tiglate . 
Total alcohols as geraniol . 

- 8° to - 11° 
23-28 per cent. 

- 9° to - 11° 30' 
26-35 per cent. 

The figures given above for Sicilian oil must be accepted with 
reserve. According to Pellini [Ann. di Clmn. A'pjMc., vii., 3), 
Pelargonium capitatum is the only species found in Sicily, and the 
following figures were obtained for four samples of oil distilled 
from the earliest to the latest period of flowering : — 





Specific gravity 





Optical rotation 

- 5.40° 

— 6.56° 

— 6.14° 


Refractive index at 25° . 





Per cent. 

Per cent. 

Per cent. 

Per cent. 

Esters .... 





Total alcohols . 






p KBF r 2r E B y 

A]] geranium oils should be soluble in Tolumes of 70 per cent, 
alcohol. The principal constituent of geranium oil is the alcohol 
geraniol C^oHigO, in the free condition to the greater extent, and 
to a lesser extent in the form of esters, of •which the tiglic acid 
ester is the principal. There is also present a notable amount of 
citronellol CjqH„pO, ■svhich, together with the geraniol and very 
small quantities of several other alcohols, makes u'p the “ total 
alcohols as geraniol." The proportion of citronellol to geraniol 
varies in the different types of geranium oil. In Spanish oils the 
citioncllol forms about 35 per cent, of the total alcohols, whilst 
in African oils only about 20 per cent, of the total is citronellol. 
In Bourbon oils the two alcohols are present in about equal 
proportions. Linalol, tei-pineol, menthol, phenyl-ethyl alcohol, 
and possibly borneol and amjd alcohol, are also present. Pinene, 
phellandrene, menthone, and citral are present, and traces of 
dimethyl sulphide (in Bourbon oils). 

Geranium oil is largely used in perfumery, very large quantities 
being consumed in the manufacture of high-grade soap. The oil 
was at one time largel}’ adulterated in a very crude fashion. 
To-day, owing to the ease with which the cruder adidterants are 
detected, adulteration is less common, and where it is practised 
it is on a more scientific basis. Palmarosa oil and artificial esters 
are sometimes used. 

E. M. Holmes (P. E. 0. R., 1913, 372) gives the following 
interesting list of hybrid pelargoniums (the majorit}’’ of which 
have had their relationships indicated by klr. J. Eraser, of Kew) 
as showing the extent to which the alteration in odour may go 
by hybridisation. The relationships of those marked with an are on the authority of Eraser ; the remainder are 
classified by E. M. Holmes. 

Weak citronellal. 

Pelargonkim adulterine m 
*Lady Mary . 

*Duchess of Devonshire . 
P. angiihsum (-f cecvllatvm) 
*Pretty Polly 

P. hlattarinm 
P. capiiatum 

*var. conspicunm . 

*Dale Park Beauty 
^Kimberley . 

*Mrs. Kingsbury . 

Eaint rose, ladanum, and 


CitroneUal, slight ladanum. 

Eaint rose, ladanum, ‘ and 


Rose, ladanum, faint butyric. 
Ladanum and pepper. 

Eaint rose and ladanum. 



PWBFU M E nr . 

'^Old Unique 
Scillonian . 
*Sliottenden_Pet . 
P. crispum. 

var. compactum 
Clyne’s Seedling . 
P. clenticulatum. 

*var. fiUcifolium 
Pheasant’s Foot . 
P. fragrans 
P. gratum 
P. graveolens 
^Little Gem 
*Monsieur Nonin . 
^Scarlet Pet 
*Westonbirt . 

P. papilionaceum 
P. pinnatum 

P. qiiercifolnim. 

Guriy . 


Danesford . 

*Fair Ellen . 

*Fau.’ Emily . 

*Miss Dorrien Smith 
Sweet Ellen 
P, quinquevulnera 
P. selechim 
P. iomenfosum. 

^Godfrey’s Bride . 
P. vitifoliwn. 

*Mrs. Babington . 

Fault rose and tansy. 

Slight rose and strong ladanum. 
Bose and citronellal. 

Bose and faint peppermint. 

Citronellal, famt rose. 

Bose and citral. 

Faint butyric and ladanum. 

Bose, ladanum and faint butyric. 
Fault rose and tansy. 

Tansy and faint nutmeg. 

Faint rose, peppermint, ladanum. 
Ladanum, slightly butyric. 

Bose, citronellal, and ladanum. 
Citronellal, slightly mousy odour. 
Bose, ladanum, and slightly 

Ladanum, faint citronellal. 

Strong pepper. 

Ladanum and faint peppermint. 

Faint citronellal, ladanum. 
Ladanum, faint rose. 

Shght citronellal, ladanum, pepper. 

Bose and citronellal. 

Peppermint and faint rose. 

Weak rose. 

GERANYL ACETATE. — ^This ester, of the formula CjqHi^. 
OOC.CH3, is of very great importance to perfumers. It is a 
constituent of many essential oils, and is used on a considerable 
scale in the manufactme of numerous artificial perfumes, especiall}^ 
those which are required to have a rose effect. It is prepared 
artificially by heating geraniol and acetic anhydride in the presence 
of sodium acetate, washing the resulting oil with water, and 
finally rectifying under greatly reduced pressure. When pure, 
geranyl acetate has the foUoAving characters : — 

Specific gravity at 0° . . 0*9388 

Specific gravity at 15° . . 0*9174 

Boding point. , . . 242°-245° 

Befractive index . . . 1*4628 at 15° 



It is not easy on a commercial scale to manufacture this ester 
in a state of absolute purity, but good-qualit}^ samples as met 
uith on tlie market should have an ester content of not less 
than 95 i^er cent., and should give figures approximating to the 
above. Geranyl acetate forms the prmcipal constituent of the 
essential oil of Evcahjpias 2Iacar{hiri (q.v.), in which it occurs, 
to the extent of over G6 per cent., associated with about 10 per 
cent, of free geraniol. 

GERANYL BENZOATE.— This ester, C10H1_.COO.CcH5, is 
used to some extent in the compounding of artificial floral bouquets. 
It is prepared by mixing 3 kg. of geraniol vdth 1-5 lig. of pyridine, 
cooling to ice temperature, and adding, with constant agitation, 
2-5 kg. of benzojd chloride, avoiding any substantial rise in 
tempcratm’e. The mixtm’e is allowed to stand for several hours 
at ordinary temperature, and the separated oil is washed, first 
with water and then with a dilute warm solution of sodium 
carbonate. The resulting oil contains unaltered geraniol, but it 
cannot be purified by rectification, as it is partially decomposed 
on distillation, even in vacuo. If, however, the product be washed 
until a 50 per cent, solution of sodium salicylate, the unaltered 
geraniol is dissolved out and the product becomes considerabty 
richer in true geran}! benzoate. The pure ester boils at 195° at 
a pressure of 15 mm. 

GERANYL BUTYRATE.— Geranyl butyrate CioH^.OOC 
(CHcla-CHg is an oil of sweet rose odour, finer than that of geranjd 
acetate, and of great value to the perfumer. It is prepared by 
heating geraniol dissolved in pyridine with butjnyl chloride, and 
is an oil boiling at 143° at 13 mm. pressure. It is used to advantaee 
in the preparation of artificial otto of rose and in many artificial 
floral perfumes. Its specific gravity is about 0'892, and refractive 
index 1'4550. 

GERANYL FORMATE. — ^This ester, CigHi^OOC.H, is one 
of the most valuable of the geranyl esters to the perfumer. It has 
not been found in any essential oil, but may be prepared artificially 
by allowing formic acid to react in the cold with geraniol in the 
presence of .a trace of sulphuric acid as a condensing agent. It 
has a fine rose odour, somewhat like that of the tea rose, or, 
perhaps, “ green rose leaves.” It is, when pure, an ofl. boiling at 
114° at 15 mm. pressure ; but it is impossible to manufacture it 
in a pure condition on the commercial scale, so that the com- 
mercial ester rarely contains more than 95 per cent, of actual ester. 



A good-quality geranyl formate should have a sweet powerful 
odour, free from any trace of “ acid ” odour, and should have the 
following characters : — 

Boiling point at 3 mm. 
Specific gravity 
Optical rotation 
Befractive mdex . 
Actual ester 

88 ° 

0- 920-0-927 
0 ° 

1- 4640-1-4665 

at least 95 per cent. 

(CHllCH^la, is isomeric with and similar in odour to geranyl 
butyrate. It is an oil which boils at 137° at 13 mm. pressure. 

GERANYL ISOVALERIANATE.— This ester has the for- 
mula CiiHi 700 C(C 4 H 9 ). It has a modified rose odour and is 
capable of imparting a very characteristic note to artificial rose 
perfumes. Its specific gravit}'- is about 0-890, and refractive 
index 1-4570. 

GERANYL PROPIONATE. — ^This ester, which is inter- 
mediate in character between the acetate and the butjT-ate, has 
a specific gravity about 0-9025, and a refractive index 1-4580. 

GERANYL TIGLATE.— This ester, CioHi^.OOC.ClCHg) : 
CH.CHg, is the characteristic odour bearer in geranmm oil. In 
the determination of the esters in this oil they are always returned 
as geranjd tiglate, which requires a different calculation from that 
for linatyl acetate. Geranyl tiglate is a liighly odorous oil "with a 
sweet rose-geranium odour. 

GINGER. — ^This highty aromatic substance finds its principal 
employment as a spice. The resinous matter and the high boiling 
constituents of its essential oil, however, have a high fixative 
value, and to a small extent it can be used to advantage in per- 
fumery. Ginger of commerce is the dried rhizome of Zingiber- 
officinale, probably a native of tropical Asia, which is largely 
cultivated in the East and West Indies, in China, in Africa (Sierra 
Leone), and to a small extent in Australasia. The method of 
cultivation in Jamaica, which produces the most esteemed ginger, 
is as follows {Bull. Botanical Dept, of Jamaica, December, 1891) : 
“ The most suitable soil for ginger culture is a weU-drained clayey 
loam. The land should be well dug and cleared of weeds. Small 
pieces or protuberances of the root, 1 or 2 inches long, are planted 
during Slarch or April, 4 inches deep and 9 to 12 inches apart. 
It is well to cover the land with a moulding of dead leaves, straw 
or litter, mixed witli manure. In a few months the whole ground 



will bo covered. The flowers appear in September. When the 
stallis wither, in the following January or February, it is time 
to dig up the roots. When the tubers have arrived at maturity 
and have put forth stems, they are fibrous, but before this takes 
place they are still succulent, and, if recpiired for preserving, should 
then be taken up. Ginger is an exhausting crop on the soil, and 
should not be planted on the same ground two consecutive years. 
The j-ield per acre is said to be 4,000 lb. and upwards.” 

Guiger rhizomes are sometimes imported in the soft juicy 
condition known as green ginger, but the ordinary gingers of 
commerce are washed, dried, and scraped (uncoated ginger), or 
are merel}' washed and dried (coated guiger). It is also sometimes 
bleached or coated uith lime to erroneously suggest bleaching. 

Sawer {OclorograpMa, ii., 95) gives the foUoiving account of the 
cultivation of ginger in India as carried on in the hill states 
adjoining the Ambalah district : — 

“ Ginger is principally produced m Mahur Massa, Patra, Darva, 
Kotlii, Kotahi, Bagal, and Jayal. The best pieces of last year’s 
harvest are selected and placed in the corner of a house in the 
month of Phagan ; the heap is then smeared over and covered 
with cow dung to keep the roots from drying up in Har month, 
w'hen the first rain falls. The land is ploughed up two or three 
times and then divided off into beds,' with a little raised edge 
round each bed, care being taken to make openings to let super- 
fluous water run off ; for if w^ater stands on the crop the roots 
will rot. Little pieces of the roots are then buried 3 inches deep 
in the soil at intervals of 9 inches, and the field is next covered 
over with the leaves of trees, w^hich keep the soil moist, and over 
the leaves is spread manure to a depth of | inch. When it rains, 
the water, impregnated with manure, filters rapidly through the 
leaves to the roots. Artificial irrigation is not employed while 
the rainy season lasts, but from Assuh to Poh it is necessary. In 
the month of Poh the plants are about 2 feet high. In the months 
of Sawan, Bhadon, and Assuh the field is weeded three times.” 

According to Ridley (” Spices,” Macmillan & Co., London, 
1912), there do not seem to be many forms or varieties of the 
plant, as mi g ht be expected from the propagation being almost 
entirely by means of cuttings. • 

The Malays are acq^uainted with three forms, which they know 
under the foUo^ving names : — 

Halyia hetul (true ginger) is the name given to a form with 
broad leaves and a very white-fleshed rhizome. It is taller than 



the other varieties, and is used for making sweetmeats and as an 
ingredient in curries. 

Halyia hara or Halyia padi {bara = hot coals ; padi = rice) is 
a smaller plant than the former, and is of greater pungency. It 
is used locally in medicine. 

Halyia Jmdang is of a redder tint than the others, and is used 
in native medicines. 

In Jamaica the planter divides the plant into “ blue ” ginger - 
and “ yellow ” ginger, so called from the tint of the rhizome. 
Blue ginger is also known as “ flint ” ginger, and the j’^ellow 
variety as “ turmeric ” ginger. According to Kilmer, the plants 
producing these varieties cannot be distinguished except by the 
tints of the rhizomes. He suggests that blue ginger is a degenerate 
form. The root of the blue ginger is hard and fibrous, and is of 
less value commercially than that of yellow ginger. 

Canton ginger, which is known in this country in the form of 
preserved ginger, appears to be a more distinct variety. The 
rhizome is thick and succident, hence its use as a sweetmeat. It 
is said that it cannot be di’ied in Canton on accoimt of the absence 
of sufficient sun heat in the season when the rhizome is dug. 
There has been a good deal of confusion as to the plant from 
which the Chinese ginger is obtained. In 1891 plants stated to 
be the source of Canton ginger were sent to Kew Gardens, and 
were identified as Alpinia galanga, but it is now established that 
these were the VTong plants, and that Chinese ginger is actually 
the product of Zingiber officinale. 

Ginger was, according to E-idley {loc. cit.), one of the earhest 
Oriental spices known to Europeans, and was certainly known 
to the Greeks and Romans. The name zingiber (ginger) is 
probably derived from the Sanskrit sangabib through the Arabic 
zanzabib. The Greeks and Romans appear to have obtained it 
from the Arab traders in the East, who doubtless brought it 
from India. Its original home is not known, as no one seems to 
have met Avith it in a wild state. The spice was well known in 
England before the Norman Conquest, and in the thirteenth and 
fourteenth centuries was nearly as common in trade as pepper. 
■'One pound was, at this time, worth about as much as a sheep. 

In the fourteenth century the Italians classified ginger in three 
forms : — 

{a) Baladi, coimtry or wild ginger. 

(6) Golumbmo, that imported from Columbum (Quilon, in 
southern India). 



(c) jlccchhis, that imported vid Mecca. 

Zd.'irco Polo is probably the first traveller who records having 
seen the plant alive (12S0-1290). He met with it in Cliina, 
Jialabar, and Sumatra. It was described in 1292 bj’’ John of 
Montecorvino, and later by Xicolas Conti. 

Preserved ginger in .syrup, or green gmger, was imported into 
Europe as a sweetmeat as early as the Jliddle Ages. As the 
rhizomes of ginger are very easilj' transported in a living state 
for considerable distances, it is not surprising that the plant was 
introduced into America very soon after the discovery of the 
Xew World, and before am’- other Oriental spice. It was brought 
to Xew Sixain (l\Icxico) by Francisco de Mendona, and the rhizomes 
were e.’cported from San Domingo as earh* as 1583, and from 
Barbados in 1G94. 

Ginger itself is not adulterated to any great extent, although 
from time to time ground ginger mixed with the powdered 
exhausted spice is found on the market, and sometimes samifies 
are found until too much mineral matter. 

Preparations in the liquid form, however, which, from their 
name, would appear to be made from ginger — such as essence 
of ginger, ginger ale, ginger beer, and similar preparations — are 
very frequently adulterated with capsicum, so that a fictitious 
strength is given to the preparation at a trifling cost. 

A. H. Allen {Analyst, xls., 124) gives the following anal3’ses for 
pure gingers : — 






















1. Total ash • • . . 








2, Ash soluble in water 








3. Alkalinity of 2 as K«0 








4. Extracted by 90 peV cent, alcohol 








i>. Extracted by proof spirit 








6, Extracted by cold water . 









I i 


K ' 
















1. Total Ash . , . . 






' 4-5 

1 — . 

2, Ash soluble in water 




, Ml 


i 1-37 

, — 

3, AlJ:alinity of 2 as K^O 






1 — 

4, Extracted by 90 per cent, alcohol 


I G-88 

i 7-86 

1 — 

1 . — 

1 — 

5. Extracted by proof spirit 


' IG-l 

! 11-8 





6. Extracted by cold water . 


I 9-8 

1 8-5 









The following analyses are due to Richardson : — 





Fixed oil, 

Starch, j 



1. Calcutta 


Percent. , 








Per cent. 


Per cent. 




2. Cochin. 








3. Unbleached Jamaica 








4. Bleached Jamaica . 








5. Bleached Jamaica . 







For the detection of capsicum in preparations of ginger, Garnett, 
Grier, and La Wall {Analyst, xxxiv., 321) recommend the follo’idng 
method. The liquid, such as ginger ale, is warmed to expel COo 
and alcohol, if present. The aqueous residue is rendered acid 
with dilute sulphuric acid and shalcen with 50 c.c. of ether for a 
minute. If the residue from the ether, which is allowed to 
evaporate spontaneous^, weighs less than 10 mg., it is treated 
witli 2 c.c. of ^ alcoholic caustic potash solution. An additional 
1 c.c. of the alkaline solution is added for each further 10 mg. 
of residue. Tlie mixture is gently heated to boiling on a water 
bath for thirtj'’ minutes under a reflux condenser. The alcohol 
is then poured off, water added, and the liquid well shaken Avith 
ether. The ether is separated and evaporated. If the residue has 
a hot pungent taste, capsicum is present. One part of capsicum 
in 10,000 parts of liquid can thus be detected. 

The essential oil distilled from the true ginger rhizome has a 
liighl 3 ’- aromatic odour, but is free from the pungent flavour of 
the spice, which resides in its resinous constituents. The rhizome 
^delds from 2 to 3 per cent, of a greenish- 3 ’'elloAA' oil having the 
following characters : — 

Specific gravity ■ . • 0-874-0-SS6 

Optical rotation . . . — 25° to — 50° 

Refractive index . . . ]‘4-S85-l*4950 

Acid value .... 0-2 

Ester value .... 1-15 

Ester value after acetylation . 30-45 

Oils AAull bo found, however, from time to time whose characters 
fall outside the above limits. Bacon, for example {Philippine 
Jour. Sci., 1910, 5, 259), examined a sample distilled in the 
Philippines which had an optical rotation + 5*9°. Japanese oil 
has been found having a specific gravity 0'894, and optical 



rotation -f 9 ° 40 '. A Java oil has been found vith an optical 
rotation -f 13 ° 9 '- 

The oil consists principally of the terpenes J-camphene and 
jS-phcllandrene, vith a sesquiterpene (or mixture of sesquiterpenes) 
laiou'n as zingiberene. Cineol, citral, borneol, methyl-heptenone, 
nomd aldeh3'de, linalol, a sesquiterpene alcohol named zingiberol, 
CisHogO, and various esters have been detected in the oil. The 
princiiDal odour hearer is probablj^ zingiberol. 

GINGERGRASS OIL. — This useful perfume oil is con- 
veniently considered in conjunction uith palmarosa oil, the so- 
called East Indian geranium oil. (See “ Geranium Oils.'’) Con- 
siderable m3’-stery has for man3" 3’ears surrounded these two oils, 
and the questions involved cannot 3*et be regarded as solved. 
So late as 1893 the authors of “ Pharmacographia Indica ” stated 
of the oil distilled from Andropogon SchccnantJms (which, however, 
is to-day renamed Cymhopogon Martini), that : “The oil distillers 
in Khandesh call the grass Moiiya when the inflorescense is young 
and of a bluish-white colom- ; after it has ripened and become red, 
it is called Sonfiya. The oil obtained from it m the first condition 
has a more delicate odour than that obtained from the ripened 
grass. The mot^a oil is usualty mixed mth the second kind, 
which, b3’- itself, would not fetch a good price in the Emopean 
market. (This ma3'- to a great extent account for the considerable 
difference in the qualit3' of the two commercial grass oils, the so- 
called geranium oil and ginger grass oil).” 

For man3’^ 3-ears gingergrass was regarded on the London market 
as merel3’’ adulterated palmarosa oil. It appears certain, however, 
that the two oils are tAvo quite different j)ure oils, and that the 
statement quoted above from the “ Pharmacograpliia Indica” is 
incorrect. The grass Cymhopogon Martini exists in two forms, 
whose botanical differences have not been made out. The nath-e 
name for the grass is Roslia or Rusa grass, and the two forms arc 
knovTi as Motia and Sofia. The motia grass yields palmarosa or 
Indian geranium oil, whilst the sofia grass 3delds gingergrass oil. 

The grass grows, according to Dr. D 3 unock, freel3>-, tliough not 
very widel3-, on open hill sides in West Khandesh, especial^ in 
Akrani. According to a report b3'- R. S. Pearson {Indian Forest 
Records, vol. v., part vii.) the most important localities from which 
Rosha oil is obtained in the Bombay Presidenc3'^ are. North, East, 
and West Khandesh, and the North and South Nasik Divisions 
of the Central Circle, and to a less extent from the Surat Dangs 
and Ranch Mahals Divisions of the Northern Circle. In these 



localities the bulk of the grass comes from the Shahada, Taloda, 
Pimpalner, and Akrani Ranges of Khandesh, while the Central 
and Northern Ranges of the Noi’th Nasik Division also produce 
considerable quantities. 

Aecording to a reijort received from Messrs. Volkhart Brothers, 
Ltd., Khandesh and Nasik were formerly the chief exporting 



Name of 

Approximate area for which 
leases are given for the collec- 
tion of Rosha grass. 


Berar ' . 



Open forests A . 220,513 
Dense forest BJ . 522,459 

' Total . 742,972 

Generally the “ Motia ” 
grass is found in class 
A and the “ Sofia " 
in class B forests. 

* > • 

j Niinav . 

j No information available, 

1 though the area is 

1 knowntobelarco. 




J > • 







I In the Ycotmal Pusad 

Alcola . 


In the Narnala block. 

1 f 



In the Morsi-Warud and 
Amraoti Ranges. 



Reserved forest | 

In the Ambara Range. 

wara J 

\ 20,000 

In Ryotwari and IMal- 
guzari lands. 


Saugor . 


Small quantities only 

> } 


Mandla . 

• • . . 

Area not knovm. 


Only a very small 
quantity of “ Sofia ” 
grass available. In 
other parts of this 
- Circle the grass is 
not available in com- 
mercial quantities. 

districts in India, but now they are of less importance than tlie 

The most important areas from which Rosha grass is obtained 
in the Central Provinces are in the ]\Ielghat, Betul, and Nimar 
Forest Di\dsions of the Berar Circle. The grass is found else- 
where, scattered in small quantities through the forest, and 
though distilled in some divisions it is not Avorked on an 
extensive scale. 



The table on p. 2GS give-s the approximate areas in eacli 
division in which leases are annually given for the collection of 
Eosha grass. 

The most important areas from which Eosha grass is obtained 
in Central India are the Ali Eajpur. Jhabua, Dhar, and Barwani 
States, of which the Jhabua State is the most important. In Ali 
Eajpur, Eosha grass is found growing in the southern and western 
parts of the State and nearlj' all over the Jhabua State, while in 
Dhar it is found in limited quantities in the Mandu, Dharanpuri, 
Kukshi, and Nananpur Eanges. In Barwani State, Eosha grass 
is found in large quantities in the Narbadda and Pati Eanges, 
and in limited quantities in the Silawad, Pansemal and Eajpur 

The areas over which Eosha grass is found growing in Ali 
Eajpur, Jliabua, and Dhar States is not known, while that in the 
Barwani State is given by the local authorities to be as follows : — 

JTnmo of 

1 i 

Name of Range. | 

area for 
which leases 
are given 
for tho 
collection of 
Rosha grass, 
in acres. 


No. of 
tons of 
grass ex- 









/Narbadda Range ' 
Pati Range . ! 

^ Silawad Range . ‘ 
Pansemal . ; 

i^Rajpiir Range . j 






} { 



These two Ranges 
are leased together. 

In 1909-10 no grass 
was available. 

In 1911-12 and 1912- 
13 no grass was 

A certain amount is also available for distillation in Madras. 

Pearson (loc. cit.) states that the local practice, which is the 
only method used at present for extracting the oil, is bj" direct 
fire-heated stills, steam stills having been used onlj’ experimentall 3 ^ 
The flower and leaf, and small portions of the stem are used for 
distillation. The flower and the upper third of the stem are 
collected in September and October, being tied into bundles or 
“ pulas ’’ of about 4 oz. each. A second cutting is frequently 
made when the grass flowers for its second time. The grass is 
either distilled in a partiall 3 ' green state, or the flower heads and 
portions of stem are carefullj* dried in the shade before distilla- 


p E li F V ii/ E n y 

tion, during Avliicli process they lose from 20 to 40 per cent, of 
their weight. The plant used by the local distillers varies but 
little from district to district, being always of a primitive tj^pe. 
The still is always erected quite close to a stream or pond, so as 
to provide plent}’’ of water for condensation puiqioses. The still 
itself is of iron or copper, and is cj'lindrical in .shape, having a 
large opening at the top for the introduction of the charge. The 
stills hold from 12 to 14 gallons, and are charged with 1 part of 
grass and 4 parts of water, and then heated over a naked fire. 
E.xperiments carried out by j\Iessrs. Pheroze & Co., of Bombay, 
resulted in a yield of 0-87 per cent, of oil by distilling the entire 
plant, which consisted of 54 per cent, of stalks, 28*5 per cent, of 
leaves, and 17-5 per cent, of flower tops. When these portions of 
the plant were distilled separately, the following yields of oil were 
obtained ; stalks, 0-04 per cent. ; leaves, 1*32 per cent. ; flower 
tops, Iwl per cent. The yield, however, is variable, and may 
reach 1 per cent, on the fresh plant, and nearly 2 jjcr cent, on the 
dried plant. 

The industry is a very important one, the annual distillation 
reaching from 80,000 to 120,000 lb., possibly even more. 

Messrs. Volkart Brothers state that Piosha oil, both “ Motia " 
and “ Sofia," is consumed all over India for tlie mahufacture of 
native “attars." Calcutta, Benares, and other places in northern 
India take as much as 3,000 to 5,000 lb. annuall}^ for this purpose, 
the oil first finding its way to Bombay, from which place it is 
sent to the north. In addition to the above quantit}^ 3,000 
to 4,000 lb. of this oil finds its wa}'’ direct to Burhanpur in the 
Nimar district, where it is made up local!}" into “ attars.” Prob- 
ably .small quantities are also retained in the producing districts 
and manipulated locally, but on this point no reliable information 
is available. 

A. D. Bhote, a Range Forest officer in the Central Pro^dnees, 
states that Rosha oil, and especially “ Motia,” is considered to be 
a good remedy for rheumatism and is sold for this piu’pose in 
most Indian bazaars. It is also used to a limited extent for 
scenting soap. The oil is considered to be a cooling astringent 
and is used in the case of headaches, for skin diseases, and is said 
to be a cure for baldness ; it is never taken internally, however, 
except in veiy small doses as a cure for bilious complaints. 

Its cliief use in India is for adulterating “ attar " of roses, 
either by dilution of the “ attar ” or by sprinkling the rose leaves 
with Rosha oil before distillation takes place. Bhote states that 


P E Ey U'M E E r 

before using Rosha oil to adulterate rose ‘‘ attar ” it lias to be 
refined ; this is done by shaking the Rosha oil with water mixed 
wiili lime juice and then exposing it to the rays of the sim. This 
is no doubt done to bleach the colour of the oil in order to make 
it resemble “ attar of roses in colour. Further, he states that 
Rosha oil which in the process of manufacture has been over- 
heated is too dark in colour for use in adulterating rose “ attars." 

Rosha oil, as found on the market in India, is rarelj’- absolutely 
pure ; in fact it is nearly always heavily adulterated with tur- 
pentine, linseed, rape, ground-nut oils, etc., the adulteration 
being often carried out by the distillers themselves. On re- 
distillation to obtain pine oil, a more concentrated and more 
strongly perfumed oil is obtained, which is, however, not often 
found on the Indian market. 

R. S. Pearson (Zoc. cit.) has made the following suggestions for 
improving the industry, and, considering that these two important 
oils are practically a monopoly of India, it is to be hoped that 
his suggestions will be acted upon : — 

It requires no very deep knowledge of the JRosha grass industry 
to arrive at the conclusion that the business is not being carried 
on to the best advantage of everybody concerned. Ever; 5 d;hing 
points to the desii’ability of introducing steam-distillation plants, 
not only in order to obtain a greater quantity of oil from a given 
quantity of grass, but to reduee the cost of production bj’- a saving 
in fuel and labour. 

Af ter carrj-ing out experiments with the steam-distiUation plant 
in the Melghat Division, the foUoving conclusions have been 
arrived at ; — 

(1) That approximately 20 per cent, more oil can be obtained 
from a steam plant than from a dii’ect-fire stiU when using 
thoroughly sun-dried grass. Again, when using steam distillation 
with dr 3 ’' and green grass, 100 per cent, more oil was obtained 
from the latter for the reason that the oil has not time to volatilise 
out of the green grass. The above are the two extremes, so that 
were a plant erected of sufficient size to work off the grass nearly 
as quickly as it came in, namely, in a partially green state, the 
5 deld, when using a steam plant, would be at least 50 per cent, 
greater than from the direct-fire stUl at present in use. 

(2) That the consumption of fuel when using a boiler is some- 
where about 100 per cent, less than that required for a direct-fire 
still, and SO per cent, less than that required when using a modified 
direct-fire still. 



(3) That the amount of labour reciuh’cd to work a steam still 
is, if anything, less than that requu'ed for a direct-fire plant, 
though the actual pay of a boiler nian, working also as an overseer, 
is somewhat greater than that of an overseer necessary to supervise 
the plant at present in use. 

(4) That the rate of distillation in all three t 3 ^pes of stills is 
about the same, though the time taken to charge and unload 
a steam or modified direct-fire still is less than that requned for a 
direct-fire still. 

(6) That better results are obtained when working at 10 lb. 
pressure in the boiler than at higher pressures. 

(6) At present mo redistillation is carried out, the colour of the 
oil being pale yellow, wliich on storage becomes darker, due to 
oxidation. When distilling with either a direct-fire or steam still, 
traces of moisture become emulsified with the oil, more so in the 
latter case. To overcome this difficulty a simple anhydrous 
sodium sulphate filter is recommended. 

(7) It should be remembered that the rectified oH is water 
white ; this can only be obtained by redistillation, which can 
onty be done by adopting the steam process. Whether redistilla- 
tion will pay depends entirely on the fluctuation of prices in the 
market. It is a pomt that should be carefully borne in mind as 
the industry expands. 

(8) That where at present only one small still is worked in an 3 ^ 
one locality — in other words, where only small quantities of 
Bosha gi’ass are available — ^it would not be worth while erecting 
a steam plant, but that far better results than those given b 3 ’' a 
direct-fire still would be obtained by using a modified direct-fire 
still fitted with a false bottom, so that the water and grass should 
not come in contact, thus introducing steam distillation on a 
modified scale, as advocated by Dunbar Brander. Wliere, how- 
ever, two spiall stills are at present worked a small portable steam 
plant is advocated, which could be moved at least once in the 
working season to another place after the grass in the first locality 
had been exhausted. The third case to be considered deals vdth 
such places as exist at the foot of the hills in the Melghat, where, 
3 "ear after year, three or more Bosha stills are erected in one place 
and where the grass is abundant. In such localities it would be 
advisable to erect more permanent plants, consisting of an S-h.p. 
boiler, four or more stills, and one condenser to ever 3 ^ two stills, 
the whole covered in by a roof for the protection of the plant 
during the monsoon months. 



(9) That the yield of oil when using a steam plant or a modified 
direct-fire still varies little when using sun-dried grass, and that 
the chief advantage in a steam plant is economy of fuel and 
facility in regulating the duration and rate of distillation. 

The characters of the Motia oil, or palmarosa oil, are very 
admirably summarised by Puran Singh, Chemical Adviser to the 
Forest Research Institute, Delna Dun {Indian Forest Records, 
vol. V., part viii., p. 4G) as follows : — 

The constants of the “ Motia ” oil have been determined by 
various chemists from time to time, but it has always been 
doubtful how far the samples examined could be regarded as 
genuine. Besides, it is not known if the oil obtained by a modem 
steam-distillation plant and subsequently refined has been put 
on the market, and if its constants have been recorded. Through 
the courtesy of Mr. C. E. 0. Cox, officiating Forest Economist, 
Forest Research Institute, Delira Dun, the writer had the oppor- 
tunity of examining crude oils obtained by steam distillation by 
Mr. R. S. Pearson, and it may not be without interest to give the 
constants of the oils as obtained in the laboratory of the Forest 
Research Institute, Dehra Dun. 

As regards the constants of the “ Motia ” oil recorded till now. 
Parry (“ Chemistry of Essential Oils, etc.,” 2nd ed., p. 182) gives 
a very acciuate summary : “ When pure the oH has a specific 
gravity of from 0'885 to 0-896, and is almost inactive optically, 
rotating from — 2° to -1- 2°, usually under 1° either way, and 
rarely up to -f 4°. (Gildmeister and Hoffman, in their “ Volatile 
Oils,” last edition, record a maximum of -f 6°.) The oil should 
dissolve in tluee times its volume of 70 per cent, alcohol. Its 
refractive index is about 1-4800. . . . The esters do not require 
less than 3 nor more than o per cent, of potash for saponification. 
The usual amount of esters present is from 10 to 15 per cent. 
The free gcraniol varies from 65 to 85 per cent. The total geraniol, 
free and combined, varies from 72 to 92 per cent.” 

Some time ago Mr. Burkhill, the then officiating Reporter on 
Economic Products to the Government of India, sent a number 
of specimens of “ Motia ” oil collected by himself from the Indian 
distillers to 3Icssrs. Scliimmel & Co., Leipzig. In their Semi- 
Anmial Report for 1910 Messrs. Schimniel <b Co. published the 
constants given in ihi tabb on p. 2'74 for these oih. 

Even these samples were not of the very best quality that it is 
possible to distil from the grass. The crude water-distillation 
method as emploj’cd by Indian distillers is hlcely to affect the 

r. 273 15 


quality of the oil injuriously. The water-distilled oil as put on 
the market is, as far as it is known, never rectified, though Parry 
mentions having met with rectified water-white Motia oil. In 
this connection it may be remarked here that, according to the 
Reports of Messrs. ScJmnmel & Co., this valuable Indian product 
is losing its reputation in Europe owing to lack of uniformity in 
the quality of the oil and to the prohibitive prices asked for it. 
Both of these complaints can be easily removed, the first by 
rectification of the oil, and the second by better methods of 
distillation. At present, in small crude stills, the Indian distillers 
cannot handle sufficiently large quantities of the fresh green grass 
in the proper season, nor can they arrange to dry and store up 
the grass for future use. By proper organisation and by improving 
the distillation plant it is possible to increase the annual Indian 


Placo of 



a D 










lit}^ in 
70 per 


Cliitar . 



-f 0° 6' 

oils (Molia 

1-47225 1 




Per cent. 


1-5 vol. 


Kumbi . 


-f 0° 5' 





1-5 ,, 


Moliana . 

Ills 911 In 

-f 0° 20' 





1-5 „ 



IlK 111' il 

-f 0° 15' 





1-5 „ 




-f 1° 20' 





1-5 ,, 


Udhala . 


-{- 0° 35' 





1-5 „ 

output of the ofi. vdthout any extra cost, as it is well known even 
to the Indian distillers that the green fresh grass has more oil in 
it bulk for bulk than the late ripe grass of autumn. These im- 
provements would go a great way to render the price of the oil 
more uniform. 

Rectification of the oils in a rectif^fing steam stiU, whether 
originaUy obtained bj’- water distillation or steam distillation, 
would give a standard uniform quahty of oil, which would make 
the detection of adulterants very easy. If these improvements 
are delayed, it is possible that the Indian trade in this article may 
be lost. 

For the purpose of this paper the following samples were taken 
for examination. These are described below, and the constants 
obtained for each are given in a tabular form on p. 276. 

(1) The crude “ Motia ” oil obtained by steam distillation from 



green grass, distilled tliree to five days after cutting, prepared by 
j\Ir. E. S. Pearson, Porest Economist. Distilled in October, 1914. 
Taken for examination from the museum of the Institute in 
August, 1915. The odour of the oil had gone bad, due to rancidity 
caused by the presence of water and other impurities. Before 
examination it was dried over anhj^drous sodium sulphate and 
filtered. The constants were determined according to the methods 
given in “Volatile Oils,” Gildmeister and Hoffman, 1st ed., 
pp. 185-195. 

(2) No. 1 rectified by steam distillation, dried on anhydrous 
sodium sulphate, and filtered ; 200 c.c. weighing 176 "grams 
were redistilled, and 175 c.c. weighing 154 grams, or 87-5 per cent, 
were recovered as a water-white, perfectly colomless oil. Odour 
good, though very slightly affected by the original rancidity of 
the oil taken. 

(3) The crude oil obtained by steam distillation from the sun- 
dried grass. In this case the grass was dried for about twenty-five 
days. It was prepared by Sir. R. S. Pearson in October, 1914. 
Taken for examination from the museum in August, 1915. The 
odour of the oil was bad ovdng to the presence of water. It was 
dried on anliydrous sodium sulphate and filtered. 

(4) No. 3 rectified by redistillation with steam, dried on 
anhydrous sodium sulphate, and filtered; 200 c.c. weighing 

177 grams gave 165 c.c. or 145 grams, or 81'90 per cent, of 
rectified oil. The colour was pale. Odour good, though very 
slightly affected by the original rancidity of the oil taken. 

(5) A genuine “ Motia ” grass oil received from Nimar and 
Baldana Divisions, in the Central Provinces, distilled by water- 
distilktion method by the Indian distillers in 1910 and stored in 
the laborato^ 3 ^ Taken for examination in August, 1915, dried on 
anliydrous sodium sulphate, and filtered. The odour was good. 
Ikry slight rancidity. Colour yellow. 

(6) No. 5 rectified by redistillation. From 200 c.c. weighing 

178 grams, onl}^ 100 c.c. weighing 88 grams, or 49-5 per cent, 
wore recovered for anal 3 -sis. Palish white ; odour good. 

(7) No. 5 rectified by redistillation. From 200 c.c. weigliing 
178 grams, 162 c.c., weighing 144 grams, or 81 per cent, were 
recovered for anal 3 'sis. Colour, pale ; odoui* good. 

Reading this table along vith the table of constants as given 
b 3 ' J/cssr^. Sc7nm7nel cO Go., the improvement in the qualitv of 
the steam-dislilled oil is evident as compared witli llic Avater- 
distiiled oil. Tlic AA'ater-distilled oil has a specific gravity of from 

276 IR— I 


0-8903 to 0-8946 at 15“ C., aud a five years old sample examined - 
at Delira Dun had a specific gravity of 0-8925 at about 28° C., 
v-hile the figure for the crude steam-distilled oil is only 0-8818 and. 

0- 8831 at 28° C. By drying the grass in sun the specific gravity 
of the oil distilled from it is slightly increased. It is remarkable 
that the old oil has given a rotation of + 5°, and the same rectified 
to the extent of 81 per cent. + 6°, while the rectified fraction, 
consisting of the first 50 per cent, of this oil, only -f 0° 16'. The 
optical rotation in this case is high; usually the oil has an 
optical rotation below 1° and, very rarely, up to -k 4° and even 
4- 6°. In this case this rare maximum has been reached, the 
slight increase over it being due to storage and oxidation due to 
it. The crude steam-distilled oils rotate less than 1°, the rectified 
being slightly more active than the crude oils. The refractive 
index should be taken as fairly constant for aU oils, being about 

1- 4700. The acid number of the crude steam-distilled oils is 
about double that of the oils when rectified, but it is generally 
less than those of the water-distilled samples. 

The next important consideration is the geraniol content. The 
total geraniol content of the crude and the rectified steam-distilled 
oils is 91 per cent., the water-distilled old oil showing only 88 per 
cent. But Messrs. BcUmmel <h Co. have recorded a total geraniol 
content of 88 to 93 per cent. Parry has recorded 78 to 92 per cent. 
This is, of course, due to the difference in the quality of the grass 
distilled, which would depend on : (1) locality ; (2) the climate 
(the total rainfall in the locality affects the quality of the oil) ; 
(3) freshness of the grass when distilled ; (4) age of the grass 
(the over-ripe grass yields inferior oil ; the “ virgin ” cuttings of 
the grass give better oil than subsequent cuttings) ; (5) the 

proportion of flowers to leaves and stem in the culms of grass 
taken -for distillation, the finest perfume being in the flowers. 
But 91 per cent, total geraniol content is usual in the steam- 
distilled samples examined. This figure may vary slightly with 
locality, but it must be admitted that the steam-distilled oils udll 
tend to be richer in geraniol than the water-distilled oils. This is 
further supported by the fact that in another place Messrs. 
Schhnmel & Go. themselves have reported the figures given in the 
table on p. 278 for four pure samples of Motia oil (Parry’s “ Chemis- 
try of Essential Oils and Ai'tificial Perfumes,” 2nd ed., 1908, p. 187). 

In these oils 92 per cent', geraniol is the maximum, and 77 per- 
cent. the minimum, while free geraniol varies from 68 to 83 per 
cent. The crude and rectified steam-distilled oils require about 


PEB F U M E B 7 

2*5 volumes of 70 per cent, alcohol instead of I'O volume required 
by water-distilled oils recorded by Scliimmel c& Co. 


Serial No, 




1 . 




2 . 


I 69-98 


3 ! ! 



4 . 



The Sofia or gingergrass oil has quite different characters from 
those above described. They are as follows : — 

Specific gravity . . . 0-900-0-955 

Optical rotation . . . — 30° to -f- 50° 

Refractive index . . . l*4:780-l-4950 

Acid value .... 2-6 

Ester value .... 8-55 

Ester value (after acetylation). 120-200 

The oil is not always soluble in 3 volumes of 70 per cent, alcohol. 

Pahnarosa oil {Moiia) contains as its principal constituent free 
geraniol, together with some geranyl esters. IMethyl-heptenone 
and dipentene are present in traces, and possibly farnesol (Elze, 
CJiem. Zeit., 1910, 34, 857). 

Gingergrass oil {Sofia) contains the terpenes dipentene, limonene, 
and phellandrene and, in addition to geraniol, periUic (dihydro- 
cumic) alcohol Cio HjgO. Carvone is also present, and an aldehyde, 
^10 HioO, of specific gravity 0-935, not yet characterised (Walbaum 
and Hiithig, ScIiimmeVs BericJit, April, 1904, 52 ; October, 
1904, 41 ; April, 1905, 34). 

Although the world’s supply of these oils is produced by India, 
samples of oil of the Motia type have been distilled experimentally 
in Java and examined by Scliimmel cO Go. {Bericht, October, 1914 ; 
April, 1915). These oils were of exceedingly liigh grade, and 
accentuate the need for an improvement in the Indian production. 
Their characters were as follows : — 

Specific gravity 
Optical rotation 
Acid value 
Ester value . 

Ester value (after acetylation) 
Total geraniol 

0- 891-0-892 

+ 0° 30' to + 0° 42' 

1 - 2 - 1-8 

94-3-96 per cent. 


PER F V }! K R Y 

Both oils are used as perfumes, especially for soap. Palniarosa 
oil is also used for the separation of geraruol {q.v.). The oils are 
exported in “ pots ” containing up to 250 Ih. of oil. 

GLOBULOL. — ^This body is a crystalline sespuiterpene alcohol 
which has been isolated from the oil of Eucahjpius globulus by 
Smith. It is a cr 3 'stalline substance melting at 88° to 89°, of 
characteristic eucalyptus odour. 

GLYCERINE. — Gtycerine is not a raw material of perfumery, 
but is used to a fairly considerable extent as an accessory to the 
perfume industry, so that a short description of it is not out of 
place. Glycerine is a trihydrlc alcohol of the formula C 3 Hs(OII) 3 , 
in which the hydroxjd groups can react with acids to form esters, 
so that three esters are possible "ndth any monobasic acid, according 
to whether one, two or tliree hydroxjd groups have reacted. 
Gtyceiine is used to a considerable extent in certain types of face 
creams, etc., and should, for this purpose, be of a high standard 
of piuity. Eor all practical purposes, it may be said that the 
world’s supply of glycerine is derived from the saponification of ' 
animal or vegetable fats, which consist of the glyceryl esters of 
the liigher fatty acids, such as oleic, stearic, and palmitic acids. 
The teclmique of fat splitting is outside the scope of this work ; 
for detailed information in regard to it, standard works on soap 
making, etc., should be consulted. 

Gl 3 ’’cerine is a colourless and hygroscopic liquid, existing in a 
state of superfusion, since when cooled to a very low temperature, 
it sets to a erj-staUine mass, especially on continuous agitation, 
or by infecting it with a ready formed crystal. When so crystal- 
lised the crystals melt at about 17°. The specific gravity of pure 
liquid glycerine is about 1*264, decreasing by the addition of 
water. Commercial gtycerine always contains a little water, and, 
in its highest degree of concentration, is sold as of specific gravity 
1*260. In the anatysis of glycerine the following points should be 
taken into account : — 

(1) Colour . — ^This should, for perfumery purposes, be water 

(2) Odour . — ^High grade gtycerine should be practically 

(3) Ash . — ^This should be very low, certainly not above 0*25 
per cent. 

(4) Strength . — Not more than 2 per cent, of water should be 

The following table of specific gravities gives the strength of 


P E B F U 31 E B Y 

pure glycerines, that is, glycerine in which the onty foreign 
substance present in more than traces, is water. In the case of 
crude glycerine, other methods of determining the strength must 

be used : — 

Glycerine present 


Per cent. 



. 1-2640 


. 1-2612 


. 1-2585 


. r2660 


. 1-2532 


. 1-2505 


. 1-2480 

Glycerine present Specific 

Per cent. gravity. 

93 . . 1-2455 

92 . . 1-2427 

91 . . 1-2400 

90 . . 1-2375 

86 . . 1-2242 

80 . . 1-2112 

Glycerine can be obtained by fermentation, but the process is 
not yet in a position to compete with soap makers’ gtycerine, but 
as fermentation glycerine is almost certaui to be of technical 
importance in the near future, it may be dealt ■u'ith briefly. The 
following details are due to K. Schweizer {Helv. Ohim. Acta, 1919, 
2, 167 ; andP. cO E. 0. B., 1919, 151). 

As early as 1857, Pasteur {Gompfes Benelux, 1857, 45, 2, 1913), 
in the course of his classic researches, had found that during 
alcoholic fermentation glycerme was formed as a by-product ; he 
obtained a yield of 3-60 to 3-64 per cent, on the sugar fermented. 
Later, Laborde showed that the amount of glycerine formed varied 
according to the quantity and species of yeast employed, and 
might reach as much as 7-76 gi-ams glycerine from 100 giams 
sugar. The quantity of glycerine obtained depends also on the 
conditions under which the yeast grows ; in a medium rich in 
nutritive matters more is obtained than m a medium less favour- 
able to the growth of the yeast. It has further been observed 
that the production of glycerme does not depend on the formation 
of alcohol, and is in no way proportional to the latter. 

P. Ehrlich considered that this trfliydric alcohol might origmate 
from certain ammo-acids, as is the case with amyl and other 
alcohols. It has also been supposed that it is formed from the fatty 
substance found as small liquid drops in the yeast cells ; but 
Buchner and Meisenlieimer {Berichie, 1910, 43, 1782) showed that 
the quantity of glycerine formed was much greater than that 
corresponding to the free fatty acids involved, and hence con- 
cluded that the glycerine of fermented liquids must have another 
origin. Oppenheimer in 1914 proved that glycerine could be 
produced by reduction of glyceric aldehyde and of dihydroxy- 
acetone ; now these two substances are formed during alcoholic 



fermentation, and indeed, according to some hypotheses, are 
intermediate products in the conversion of sugar into alcohol. 
It seemed possible, therefore, that by acting upon these com- 
pounds by a reducing agent at the moment of formation, they 
could be ehminated from the fermentation cycle in the form of 

The greatest difficult}^ was to find a species of yeast which 
could live in the presence of large amounts of salts, yeasts being 
usually very sensitive organisms. This difficulty was only over- 
come b}’ using a commercial pressed yeast prepared with molasses, 
which gave satisfactory* results. It was necessary at the same time 
to find a reducing agent wliich would not present the gro%vth of 
the yeast. 

For the study of acid reduction Schweizer made the following 
experiment : After having sterilised a solution of 64 grams of 
saccharose in 200 c.c. of water, he added 1 gram of ammonium 
sulphate (to supply the nitrogen necessary for the growth of the 
yeast), and 26 grams zinc powder as reducing agent. After 
making the mixtm’e feebly acid with dilute sulphuric acid, ho 
fermented it vith 6 grams of pressed yeast. During the whole of 
the fermentation the mixture was kept shghtly acid, and the 
temperature was not allowed to fall below 25°. An analysis at 
the end of the fermentation gave : — 

Sugar . . .32 per cent. 

Acidity . . 20c.c.neutrahsed 0'26c.c.normalNaOH. 

Soerensen number. 10 c.c. corresponded to 3-6 c.c. N/10 


The initial temperature was 27-5°, but after six hours it had 
fallen to 25°, and the yeast had not grown appreciably. With a 
view to assisting the growth, he added 0-5 gram of ammonium 
hydrogen phosphate, OT gram of magnesium sulphate, and a trace 
of potassium sulphate. The following figures were then 
obtained : — 

Sugar . . .32 per cent. 

Acidity . . 20 c.c. neutralised 0-28 c.c. normalNaOH. 

Soerensen number. 10 c.c. corresponded to 3'S c.c. N/10 


It was ten hours before the fermentation commenced, slowly*, 
without becoming energetic even after twenty-four hours. 

The fermentations under these and similar conditions were very 
incomplete, and it was necessary’- to abandon reduction in an acid 


P E B F r il/ E R y 

Yeasts cannot live in an alkaline inedinm, and it remained, 
therefore, to attempt the reduction in a medium kept as neutral 
as possible. These conditions are fulfilled, hj’’ the use of sodium 
sulpliate in the presence of powdered chalk. Tor example, 
04 grams of saccharose were dissolved to give a 14 per cent, 
solution, to which, after sterilisation, were added 0-1 gram 
ammonium sulphate, Od gram of ammonium hydi’ogen phosphate, 
0-1 gram of magnesium sulphate, and finally some powdered 
calcium carbonate. The mixture was fermented Avith 0 grams of 
yeast, the temperature being kept at about 30°. The yeast 
begins to develop after four hom’s. J\Ieanwhilc, a solution of 
10 grams sodium sulphite, 0-8 gram ammonium sulphate, and 
0-8 gram ammonium h3^drogen phosphate in 120 c.c. of Avater was 
prciDarcd. EAmry half hour 5 c.c. of this solution AA'ere added to 
the fermenting liquid, until all had been introduced. A very good 
fermentation resulted, Avhich was complete in tAvo days. In spite 
of the chalk, there Avas produced an acidity of 0-G c.c. N-acid per 
20 c.c. liquid. 

Having thus discovered a suitable reducing agent, the influence 
of concentration on the course of the fermentation AA'as studied, 
and for this the folloAA’ing solutions Avere used : — 

(1) Sugar solutions 20 per cent, and 5 per cent. 

(2) HutritiAm solution ; 2-5 grams ammonium sulphate, 2-5 
grams ammonium h 3 ’'ch’Ogen phosphate, and O-S gram magnesium 
sulphate ; dissolved in Avator and diluted to 300 c.c. 

(3) Reducing solution : 17 grams sodium sulphite in 100 c.c. 

Each solution Avas sterilised by heating on the AA'ater bath 
during a night, and, after cooling, 5 grams of j’east were added for 
each experiment. 

A. — 20 per cent. Sugar Soluiion. 


Per cent. 






1st daj’’ 



30 c.c. 

20 c.c. 

2nd „ 

3rd „ 



30 „ 

30 „ 

4th „ 



25 „ 

20 „ 

5th „ 


25 ° 

30 „ 

25 „ 

6th ,, 




PE EF U 31 E E Y 

Tims, in all there were added llo c.c. nutritive solution and 
95 c.c. reducing solution for an initial volume of 500 c.c., which 
had increased by the sixth day to 670 c.c. The growth of the 
yeast was not vcr}' rapid. The gl 5 'cerine was determined by the 
method used for its estimation in wine ; 100 grams sugar gave 
4*5 grams glycerine. 

B. — 5 per ce7it. Sugar Sohtdon. 


__ . _ 

Per cent. 






1st daj' 



20 c.c. 

2nd ,, 


I ““ ^ 



3rd ,. 



30 „ 

30 „ 



26° i 

25 „ 

20 „ 

5th . 


25° i 


The sugar was determined, as in the previous experiment, by 
Balling’s saccharimeter. The density of the liquid had increased, 
owing to the salts added and the fermentation products. The 
nutritive solution added was 85 c.c. in all, the reducing solution 
70 c.c. The growth of the yeast was fairty good, but was much 
slower by the fourth day. The volume, initially 500 c.c., increased 
to 630 c.c. While the more concentrated sugar solution gave 
0-67 gram glycerine per 100 c.c., the dilute sugar solution was 
found after fermentation to contain 0*32 gram gl 3 'cerine per 
100 c.c. The 3 'ield is thus 8-0 grams gtycerine from 100 grams 
sugar. High concentration is therefore unfavourable to the forma- 
tion of the trihj'dric alcohol. 

But j-iclds of this order are obtainable bj’’ simple biological 
processes in the absence of any special reducing agent. It was 
therefore necessary to make new experiments in the presence of 
larger quantities of sulphite. To this end 40 grams saccharose, 
2 grains ammonium lydrogen phosphate, and 1 gram dipotassium 
phosphate were dissolved in 400 c.c. water, and the solution 
introduced into Haj-duck’s apparatus for the determination of 
the fermentative power of yeasts. Having added 10 grams pressed 
j-east, the fermentation was allowed to become appreciable, and 
then 30 grams sodium sulpliitc were added. After twenty-four 
hours the fermentation was finished. An intense odour of Vanillin 
was given off by the solution. The COg evolved was about 



800 C.C., and 100 grams sugar had given 21*30 grams glycerine 
(mean of several experiments). 

Certain biological reactions of j’-east are accelerated by the 
presence of oxygen, and it appeared of interest to discover whether 
that were the case with this fermentation. As in the preceding 
experiment, there v'cre introduced into a Hayduck’s apparatus 
a solution of 50 grams saccharose in 600 c.c. water, and 10 grams 
pressed yeast, 30 grams sulphite being added in three portions ; 
1,820 c.c. COg were evolved, and the fermentation, without 
aeration, was finished in twenty -four hours. The final volume 
was 520 c.c., and a determination of the glycerine present gave 
9-36 grams, corresponding to a yield of 18-72 grams from 100 
grams sugar. 

An exactly similar experiment was performed in a wash-bottle, 
into which was passed a ciu-rent of sterilised air. After the fer- 
mentation the volume of liquid was 630 c.c., and the amount of 
glycerine 0-75 per cent., corresponding to a jdeld of only 9*44 
grams glycerine from 100 grams saccharose. Without aeration, 
therefore, twice the amount of gl 3 ^cerine is obtained. This result 
was to be expected, since aeration favom-s oxidation, and thus 
prevents the reduction of the gtyceric aldehj^de and the dilij’-- 

It was by this sodium sulphite method that glycerine was 
prepared on a commercial scale during the war by certain 
belligerent countries. 

GLYCERYL ACETATE. — Gtycerine C 3 Hg(OH) 3 , being a 
trihydi’ic alcohol, forms three acetic esters ; glycer 3 d monoacetate 
{monacetin), gl 3 "ceryl diacetate {diacetin) : and gl 3 ’-ceryl triacetate 
{iriacetin). Frequently the triacetin of commerce contains some 
of the other two esters. This substance has no legitimate use 
in perfumer 3 '', but is often used as an adulterant of ester- 
containing oils, such as bergamot oils. For its detection, see 
“ Esters, Artificial, Detection of.” 

GOLDEN ROD OIL. — ^Various species of solidago, of which 
the best know is Solidago odora, yield up to 1 per cent, of an 
odorous essential oil contaming up to 75 per cent, of rheth 3 d- 
chavicol. The oil has a specific gravity 0-937 to 0-960 ; optical 
rotation, 7° to -j- 14° ; refractive index, 1*5050 to 1*5160 ; 
ester value, 6 to 10 ; and ester value after acetylation, 18 to 25. 
The oil known as Canadian golden rod oil is the product of Solidago 
Canadensis, and consists almost entirely of terpenes. The oil has 
little value in perfumer 3 ^ 



GOUFT, OIL OF. — ^The Algerian plant Arlemisia cam- 
2 )estris, var. odoratissirna, jnelds an essential oil ■vrhicli is known 
locally as oil of gouft. It was originallj’- examined by Jeaneard 
and Satie {BiiU. Soc. Cliim. (3), 1904, 31, 478), and later by 
Rourc-Bcrlrand Fils {Bulletin, 1920, 4, i., 27). It is an odorous oil 
containing geraniol, gerain'l acetate, and pinene (probabty also 
nopinene). The follo^ving are the characters assigned to it by the 
investigators mentioned ; — 

Jeaneard and Satie. 


Specific gravity 

0-872 at 9-5° 

0-8763 at 15° 

Optical rotation 

— 15° 20' 

— 16°24' 

Acid number .... 



Ester number 



Saponification number 
Saponification number (after 






Total alcohols as geraniol 

11-9 per cent. 

11-65 per cent. 

Free alcohols as geraniol 

8-36 „ 

3-44 „ 

[Note that the table of characters on page 291 of Volume I. of 
the writer's work, “ The Chemistrj’’ of Essential Oils, etc.,” 
4th edition, are assigned to this oil through the accidental mis- 
placement of the last two lines on page 290. Tliis table belongs, 
in fact, to the oil of Artemisia herha alba, var. genuina, “ Scheih 

GRAINS OF PARADISE.— Grains of Paradise are the 
pungent aromatic seeds of Amomum Melegueta, a plant allied to 
ginger ; the seeds have an odour recalling that of galangal. It 
is possible that other species of amomum are used for the 
collection of these seeds. The plants are natives of West Afriea, 
where they are more or less cultivated, and are also found in the 
wild condition. The seeds, which were at one time known as 
2Iclegetce, owe their name to the native name, corrupted from 
“ JIalaga,” meaning “ pepper,” or possibly to the word Melle, 
the name of an empire in the Niger country, which maj' itself 
have the same origin from “ Llalaga.” These seeds are also known 
as guinea grains or melegueta pepper. It is not an injurious drug, 
but in the reign of George III. an Act was passed forbidding any 
brewer to have it in his possession or to use it in making beer, 



tinder a penalty of £200 ; and forbidding any druggist to 
to a brewer, under a penalty of £500. 

The seeds yield from 0*3 to 0-75 per cent, of essential oil, 
a specific gravity about 0-894 ; optical rotation about 
and refractive index, 1-4912. Its ester number is about 40, 
ester number after acetylation about 64. Its constituents 
not been investigated. 

There are a number of oil-yielding grasses found in India 
Cejdon, and, to a smaller extent, some of them in the Ma. 
Peninsula, Java, and other places, whose essential oils are of th 
highest importance to the perfumer. Some of them have no 
yet been exploited commercially, and may have considerab- 
value when they are more available to the perfumer. All of these 
belong to the tribe Andropogoneos, which is very rich in aromatic 
species. All of those which yield essential oils obtainable in 
commerce wfil be found described under their respective headings, 
such as “ CitroneUa Oil,” “ Gingergrass Oil,” “ Lemongrass Oil,” 
“ Vetivert Oil,” etc. There has, however, been a complete 
re-examination of the botanical relationships of these plants by 
Dr. Stapf [Kew Bulletin, No. 8 of 1906), so that the following maj’ 
be accepted as the present state of our knowledge on this subject : — 

According to Stapf, the aromatic character of some of these 
grasses is so pronounced as to have attracted the attention of 
man at a very early period of his history. They found a place 
in the performance of religious rites, among domestic medicines, 
in the dispensaries of the medical practitioners, and in the 
department of spices and perfumes. The Schoenantlius of the 
Ancients, the Viranam of the Vedhas, and the Sereh of the 
Malays are illustrative instances, and there is very little doubt 
that the much-discussed Kalamos arotnaiikos of the Greek writers 
was a plant of the same category, although we have not so far 
succeeded in fixing the species. With the discovery of more 
powerful or more pleasant aromas these oil-grasses gradually lost 
their importance or even fell out of use. But in our own day 
the highly perfected art of perfumery has seized on them again, 
has revived the taste for their odours, and created that demand 
for their oils which has found its response in the development 
of a regular oil-grass industry in Ceylon, India, and to a less 
degree in the Malay Peninsula and in Java. Out of the twelve 
grasses described here, the genus Gymbopogon claims ten, and 
Vetiverm and Andropogon contain one each. 


PE nr u 31 E R }■ 

(1) Cymhopogon Schosnantlnis was the Andropogon Sclw:nanthus 
established by Linnasiis in the first edition of liis “ Species 
Plantarum ” in 1753. This plant is knoma as camel grass or 
izhhir (Arabic), or hliavi (Hindustani). As it is the Hcrha 
Scltccnantlii of the ancients and the foundation of the species, the 
following history, due to Stapf, is of interest : — 

When in 1881 Emil Brugsch Be}'’ discovered the tomb of 
Dcir-el-Bahari in the necropolis of Thebes, the secret vault which 
contained the coffins of so many illustrious kings also yielded a 
remarkable profusion of botanical treasures : funeral VTeaths 
which the Icings of the Twentieth or Twenty-first D}masty (be- 
tween 1200 and 1000 B.c.) had deposited on the sarcophagi of their 
predecessors, offerings of fruits, lichens, bundles of a grass {Desmos- 
iachya hipinnaici), and quantities of the straw of another grass, 
which Professor Schweinfmrth recognised as Gymnanthclia lanigera 
(a rarely used sjmonym of C. SchosiiantJms). Some of the in- 
florescences were still in excellent condition. Even “ the odour 
of the grass was preserved to a certain extent in the mixture of the 
offering.” So early begins the history of the grass. Then the 
grass was found under similar conditions in the tombs of the 
cemetery of Hawara, in the ra}nim, again associated with Desmos- 
iachya bipinnaia. According to Professor Flinders Petrie, some 
of the tombs were probably of the Twentieth, Twenty-sixth, and 
Thirtieth Dynasties, but most were Ptolemaic. According to 
Loret, the grass is also frequently mentioned in hieroglyphic 
perfumery recipes as “ Aetluopian cane,” “ rush of the Sudan,” 
and “ C}’perus of the West.” Whether all of these names actually 
refer to C. Scliapianthus or not, the finds of Deir-cl-Bahari and 
Hawara afford, in any case, indisputable proof of tlie high place 
which was assigned to the grass 3000 years ago. To-day 
C. SchccnanfJnis does not grow in the neighbom-hood of .old 
Thebes or in the ra}mm ; it has, in fact, vdth one exception, 
never been observed in the Nile Valley north of the Baiuda 
Desert (16° to 18° N.), the exception being some specimens 
collected by Bove in the desert near Cairo in 1829. Schweinfurth 
identified the Andropogon of Deir-el-Bahari more particularly 
with the article which nowadays is brought down from the Sudan 
and sold in the bazaars of Cairo as a medicinal drug under the 
Arabic name mdharch. 

It has been suggested that the EcineJi bosetn or Kanch hailobh, 
the “ good ” or “ fragrant ” reed of the Bible, was also C. Schcc- 
7ionfJn!-s. It may, of course, be assumed that the old Hebrews 



knew the grass ; but how far it answered to those terms is difficult 
to say, considering the vagueness of the passages in which they 
occur. It was known to Hippocrates under the name Schomos, 
under which name it was often used in medicine. It is quite in 
keeping vdth the general character of Greek and Roman literature 
that one does not meet with any serious attempt at describing 
the herb schoinos. In fact, the only reference to it wliich con- 
tains a descriptive element is in Dioscorides, where he gives 
instructions for the selection of the material : it is to be fresh, 
reddish, many -flowered, purplish and whitish ..when spht apart 
{i.e., when the leaf bases, which are purphsh and wliite, are 
pulled apart), to emit an odour lilre roses when rubbed in the 
hand, and to have a hot, pungent taste. The use of the drug 
continued in the West after the downfall of the Roman Empire, 
although apparently only for medicinal purposes, through the 
Middle Ages, and even into the eighteenth century, when it 
gradually became obsolete. We And it in the prescriptions of 
Aetius (a.d. 450 ), and in the writings of the School of Salerno. 
Here the name Palea camelorum may have originated. At least 
it is attributed to Matthasus Platearius (about the middle of the 
twelfth century) in the various editions of the “ Ortus Sanitatis,” 
although it may, of course, be much older, as Galenus had already 
connected the Sclicenanthus with the camel. In the “ Ortus 
Sanitatis ” we also And the flrst flgure mtended to represent the 
Schosnantlms or Sqitinanthus, as it is called there. It is so con- 
ventionalised as to be umncognisable. Erom Brunfels (a.d. 1536 ) 
onward it is a standing article in aU the herbals of the sixteenth 
and seventeenth centuries, and is the subject of sometimes 
elaborate discussions in the commentaries on Dioscorides, Plinius, 
and Theoplnastus. It was very frequently flgured in those works, 
the flgures behig drawn from the mostly barren leaf tufts as they 
reached Europe. Sometimes inflorescences more or less con- 
ventionahsed were added. One of the earliest of those flgures, 
by Lobel (a.d. 1576 ), is among the best. A very good description 
of the drug was given by Job. Bauhin (a.d. 1658 ). Einally, in 
1692 , we have Plulcenet’s description and figme. Both are 
indifferent ; but they are supported by Plul^enet’s original 
specimen, which still exists in his herbarium at the British 
Museum, and is the typical ScliosnantJms of the old herbalists. 
On this, and on this alone, Linnaeus based the Lagurus of his 
“ Materia Medica,” which is the backbone of the Andropogon 
Sclicenanthus of the “ Species Plantarum.” The Nabataean Schce- 



nanilivs vras, in tlie times of Dioscorides and Plinius, more valued 
than any other. It was called Nabataean more lilcely because 
it came rid Nabataja than on account of its growing there. In 
connection with this, it is interesting to note that, according to 
Me\-er, Qutsami’s “ Book of Nabataean Agricultiu-e ” actually 
enumerates Idshir {Izkhir, the Arabic name of Sclmnantlms, qua 
drug), but with the epithets “ Babylonian ” and “ that of Hedjas,” 
and not as Nabataean. Mej’cr quotes from Ibn Alawwam’s “ De 
Agricultura,” who in turn quotes largely from the Arabic trans- 
lation of Qutsami’s work, which was probably vvitten in the 
second or tliird century. 

Isliag Ben Amran of Bagdad (died a.d. 903 or 905) mentions 
the Hedjas as the country producing the best Izkhir. It comes 
next to that of Antiochia, ' wliilst the African is the worst. The 
Izhhir of Antiochia is evidently the “ Babylonian ” variety, 
Antiochia being merely the market whence it was distributed. 
Avicenna (a.d-. 980-1037), too, distinguishes two kinds, the 
Arabian and an inferior “ foreign ” {ajami) kind. As may be 
expected, there is more freedom in the way in which the Arab 
•nwiters treated the subject, as some of them must have known 
the gcass in the field, or, at any rate, had first-hand evidence. 
Thus Abu Hanifadt (died a.d. 895) gives a description of it 
which could only have been made from autopsy : “ Izhhir is a 
plant with a root deep down in the ground and slender, very 
fragrant culms, like rush or papyrus, but finer and with smaller 
joints. It has tufted infructescences (fruits) like the panicles of 
the reed, but more delicate and smaller. It is pounded and 
mixed vdth perfumes. It rarely grows solitary. Where it has 
settled, it may be seen to spread and cover the ground ; it inhabits 
plains and desert land. When it dries up, it turns white.” Like 
the old Greek doctors, the Arabs prescribed it for the preparation 
of unguents, theriacs — among them the famous Elecluarimn 
Mithridatis — and oils. Ibn Baithar quotes from the “ Books of 
Experience ” the method of preparing the latter, thus : “ Take 
of the fiowers of the grass, put them in double the quantity of oil 
of unripe olives . . . press the whole well and throw the fiowers 
away ; take another lot of fiowers and put them in the oil. Repeat 
this three times in the hot season.” From the Arab vviters the 
drug passed naturally into the Persian pharmacopoeias, as, for 
instance, the “Ulfaz Udwiyeh” of Mohammed A' dullah Shirazi 
(a.d. 1450), and the “Pharmacopoeia Persica” of Prater Angelus 
(a.d. 1681). YiTience the Persians got their supply of Izkhir is 

V 23a 10 


not quite certain. So far tlie grass lias been found only in a few 
localities in Persia, and nowhere in quantity. It was probably 
mostly Arabian. Still Kaempfer speaks of a Persian and an 
Arabian SchcenantlmsP Considering the part which Arabian and 
Persian doctors played at the courts of the Mahometan princes 
of India, it would be surprising if the ingredient of so many 
theriacs, electuaries, and other preparations had not also found 
its way into the Indian dispensaries. W^e possess a fairly full 
account of an instance of import of IzlcMv under rather remarkable 
cii'cumstances in Garcia de Orta and Acosta. This is what Orta, 
in Clusius’ edition of the Aromata,’’ says : J^incus odoratus 
gi’ows in great abundance in the Ai’abian provinces of Mascat and 
Kalhat. The natives call it Sctchhar^ some also Hcixis ccicJiulc 
{JicisJiish gliusuV)^ that is, lotion grass . . . and the flowers Focci, 
. . . With the Indians no special name has arisen ; but they 
dub it Mascat grass, some also Mecca grass, and also camel hay. 
There are in those countries plenty of asses, mules, horses, etc., 
which know no other fodder. ... It is imported into India for 
medical purposes ; but the greatest quantities come with the 
horse dealers (of j\Iascat and Kalhat), who take it tied up into 
bundles with them in their ships to use it as litter for their 
horses. ... I remember that at Din they sold many bundles of 
Jiincus for a mere trifle . . . but the natives do not appreciate 
it, as they are a rough and savage people, and they do not use 
it.. We, however, and the Arab and Persian doctors employ it.’’ 
The influence of the Persian phj^sicians and the reputation of 
their pharmacopoeias were sufficiently weighty also to transfer 
the foreign name, Izichir, to the native drug. Not only was, and 
still is, the G. Schceiianthiis of the Panjab sold in the bazaars as 
IzIcJiiv, but the name has also passed on, with or without the 
qualifying epithet, ajami (foreign) ov Hindis to V etiveria zizanioides 
(A, Tnurioatus) and other indigenous aromatic grasses, so that it 
has become with certain writers almost a generic name. Thus 
the Izlchir of the Abir IzJchir of the Ain-i-Akbari (end of the 
sixteenth century) is F. zizanioides ; the Taleef Sherif ” has 
gundheel {0. Martini) as synonymous with Izlchir^ and the author 
of the ^ Makhzan-ehAdwiya ” (a.d. 1771) enumerates no fewer 
than six Hindi synonyms for Izlchir^ most of them vernaculars 
of G. Martinis It will be seen that the vernacular synonymy of 
G. Schcenanthns was, in India at any rate, just as confused as 
the scientific nomenclature of the species was up till recently. 

(2) Gyivho'pogon Iwarayicusa . — ^This gra^s first became known 



tliroiigh a piil)Iication on the Kardns Indica, or spikenard, in 1790 
by Blanc, avIio gives the following account of its discover 3 ' b3>- 
his brother : — 

Travelling with the Xabob Vizier on one of his hunting 
excursions towards the northern mountains, I was surprised one 
da 3 ', after crossing the Eiver Rapt 3 ', about twent 3 ' miles from the 
foot of the hills, to perceive the air perfumed witli an aromatic 
smell ; and. on asking the cause, 1 was told it proceeded fronr 
the roots of the grass that were bruised or trodden out of the 
ground b 3 ' the feet of the elephants and horses of the Nabob’s 
retinue. The country was wild and uncultivated, and this was 
the common grass which covered its surface, growing in large 
tufts elose to each other, veiy ranlc, and in general from 3 to 
4 feet in length. As it was the winter season, there was none of 
it in flower. Indeed, the greatest part of it had been burned 
dovm on the road w'e went, in order that it might be no impedi- 
ment to the Nabob’s encampments. I eollected a quantity of 
the roots to be dried for use, and earefull 3 '- dug up some of it, 
which I sent to be planted in my garden at Lucknow. It here 
throve exceedingly, and in the rain 3 ^ season it shot up spilces 
about 6 feet high. ... It is called by the natives Teranhus, 
which means literally in the Hindu language ‘ fever restrainer,’ 
from the virtues the 3 ’- attribute to it in that 'disease. ... It is 
esteemed a powerfrd medicine in all kinds of fevers, whether 
continued or intermittent. The whole plant has a strong aromatic 
odoiu ’ ; but both the smell and the virtues reside principall 3 ^ in 
the husly' roots, which in chewing have a bitter, warm, pungent 
taste, accompanied with some degree of that kind of glow in the 
mouth which cardamoms occasion.” 

It was believed to be the spil^enard of the ancients, but this 
is probabl 3 ' not true. The spelling of the name vlth an “ i ” 
obscures its derivation, which is from jti-am (fever) and anhusa 
(the hook used by elephant drivers to restrain their elephants). 
The name thus means “ fever restrainer.” 

(3) Cymlopogon Nardns . — This grass is that producing the 
well-known citronella oil. Early botanists believed it to be the 
Nardns Indica of the ancients, so that Linnasus gave it the name 
Avdrojwgon Nardvs. 

The citronella gi-ass early shared the fate of the other aromatic 
Andropogonco: by becoming almost hopelessl 3 ' confiLsed. It was 
Ainslie who first (1813) suggested that it was identical with the 
“ gingergrass ” of Courtallam {G. jlexnosits) and tlic cultivated 





“ lemongrass ” [ 0 . ciimtus), and it seems to have been known for 
a long time loy the latter name ; hut as “ lemongrass ” was very 
generally put dowm as Andropogon Scho&nantlms, eitronella was 
also frequently referred to by that name, ehiefly by pharmacists 
and chemists. Then, the French name for “ lemongrass being 
citronelle, the latter term also found its way into English literature, 
origmally as a synonym of “ lemongrass ” in the wider sense, and 
later on more especially of the “ Ceylon lemongrass,” that is, 
G. Nardus. Perema (1850) seems to have been the first to use 
the term “ citronelle oil ” as equivalent to “ lemongrass oil.” 

J. Bell, in his notes on the London International Exhibition 
of 1851, mentions “ oil of cintronelle, or oil of lemongrass.” He 
stated that it v^as imported from India, " and is the produce of 
a grass known to botanists as Andropogon ciiraium, and by some- 
persons considered to be identical with Andropogon SchmnanthusP 
In the Ceylon Catalogue of the Parish Exhibition of 1855, p. 17, 
we find two distinct oils : (1) lemongrass oil, from A. Schce- 
nantlms, and (2) “ eitronella oil ; citron oil ; perfumery,” and 
agauist the latter there is in the Kew copy an entry in Alex. 
Smith’s handvTiting: “ Citronella oil, AndroptogonP W. S. 
Piesse, in his “ Art of Perfumery,” 1855, p. 31, also refers to 
“ eitronella,” sajnng : “ Under tins name there is an oil in the 
market, chiefly derived from Ceylon and the East Indies ; its 
true origin we are unable to decide. In odour it somewhat 
resembles citron fruit, but is very inferior. Probably it is procured 
from one of the grasses of the Andropogon genus.” Gladstone 
(1872) and C. H. A. Wright (1874) were the first to examine, under 
the name of “ citroneUa,” the oil of G. Nardus, as is evident from 
then descriptions of the oil, but both referred it to Andropogon 
SchcBnantJms. Even as late as 1880, it was confused with G. 
flexuosus and G. ciiratus by Bentley and Trimen, who figured a 
specimen of the former as Androptogon Nardus. In 1883 
“ eitronella ” was at last clearly confined to Androjiogon Nardus 
by Watt, who gives the average exportation of eitronella from 
Colombo as amounting to about 40,000 lb. ; the exact return for 
1864 was 622,000 oz. 

Outside Ceylon A. Nardus has been in cultivation for some 
time in Penang, whence eitronella oil is mentioned as early as 
1872 by Gladstone, and in the Straits Settlements and Java. 
When it was introduced into the Malay Peninsula and Java is 
uncertain, but it cannot have been very long ago. McNair, in his 
book, “ Perak and the Malays,” 1878, p. 73, speaks of “ the 


PERFU jfE 7? 

iloiiri-'lunir growth of cilronclle and lemongra.-^?, from which 
o'-^cnti.d oil*^ are extracted, as worth mentioning t but in 18S0 
C.*Uul'*y complain^ of the insufficient attenlioii which the cultiva- 
tion of tliC'^c two grasses receives in the Straits, and in 1000 the 
total area of citronclla estates in the peninsula was estimated at 
only acres at the liighest. In Java it is mentioned by 

Itoin burgh in IS 02 as Pocmpoc! .‘^axh ivangi under A, Jirarancvsci, 
and is staled to have been introduced into tlic Cultuurtuiii 
in ISOL He drew tlie attention of Scliiinmel & Vo, to tlie oil 
])ropared from the Javanese crop : this reference event ualh" led 
to tlie establishment of citronella distilleries in Java. According 
to Gildemcister and HofTmanii, both the Mala^’ Peninsula and 
the Java grass rci^rescnt the Jllaha Pengiri variety (sec below). 
Quite recenth" experiments in growing citronella grass have been 
made in the West Indies. 

Two kinds of citronclla grass have recently been distinguished 
b}^ the growers : il/a//a Pengiri (the Great Pengiri), and Lenabedu 
or Lana Batii Pengiri, or, briefly, LenahaUi, The former is also 
known as “old citronella grass,’’ or “Winter’s gi*ass,” because 
it is now almost exclusively grown hy Messrs, Winter & Son ; the 
other is spoken of as “ new citronclla grass.” Specimens of both 
varieties received at Kew from Galle, so far as they go, do not 
show any moriffiological differences. The old citronclla grass is 
described as a surface feeder, which soon grows out of tlie ground 
and gets exhausted, dying off after ten or fifteen 5 'ears of cultiva- 
tion : and it has somewhat broad leaves, and tlie bushes formed 
are larger than the second (i’.c., Lenahatu), It fields a finer oil, 
but the necessit}’' of freq^uent replanting has led to its being more 
and more replaced by the Lenahatu variety". 

6 b Kerdns in its t 3 ’pical form is onlj* known in tlie cultivated 
state. It is an auTiless gi'ass, the valve or flowermg glume of the 
hermaphrodite spikelet being either entire or more or less bifid, 
with a minute point or a very^ fine and short bristle from the sinus. 
The flower.s are usually apparently normal, but do not seem to 
set freely, and in some cases all the spikelets are male or otherwise 
im])erfccl]y developed, or they' are infested with Usiilcigo, On 
tlie whole, the reproductive sy^stem seems to be debilitated. This 
is tlie case with all tlie specimens I have seen, irrespective of their 
origin, and is evidently' the result of the treatment the grass has 
experienced from the grower, in whoso interest it is that they' 
should not flower, as, according to Gildemcister and Hoffmann, 
“ otherwise tlie tufts become too dense, become yellow uitlun. 



and spoil.” Stil], a certain amount is allowed to seed for renewing 
the plantations, the nsual mode of propagation being apparently 
b}’’ dividing the bushes. The reduction or suppression of the awn 
is no doubt in correlation vith tlie partial sterility of the cultivated 
C. Nardvs, the wild ancestor of v'hich we have to seek among the 
awned forms. It has very generally been assumed that the 
citronella grass is a descendant of the wild Mcma grass of the 
Ceylon Patanas, but it is unfortunate that there is no specimen 
at Kew which is definitcl}’- stated to have been collected in the 
wild state. Sir Josej)!! Hooker, however, vlio had the grasses of 
the Peradoniya herbarium at his disposal when working out the 
GrammecG for Trimen s “ Handbook of the Plora of Cej'^lon,” says 
that there wore three specimens of the wild Mc7?i(2 in that collec- 
tion from Galle, Mao 3 ’a, and Peradenij'a, and thej’- were all 
Hackcl’s AndrojJogon Nardus, var. nilagiricus. Willis also states 
that the Manu of the is distinct from the cultivated 

citronella grass, but docs not sa}' how it dilYers. Now there is a 
Hew a suite of excellent specimens of the cultivated awnless 
0. Nardus from I\rr. Jowitt’s estate at Bundarawalla, and, sent 
with them at the same time and from the same localiCv, and 
numbered concurrently with the first, is another set which is 
undoubtedly Andro 2 )ogon A^ardus, var. mlagiricus. Whether 
thej’- grew wild on the estate or Averc in cultivation is not stated. 
A careful comparison of both sets has convinced mo that this 
Andropogoii Nardus, var. mlagiricus, is, as »Su’ Joseph Hooker 
has stated, actuall}’- the mother plant of the Peugiri Aland, or 
citronella grass. Gildomcistor and Hoffmann state, on Mr. 
Winter’s authoritj’-, that the AlaJia Pengiri came from jMalacca. 
As the citronella grass is a comparative^ recent introduction to 
the Malay Peninsula, and certainly does not occur there in the 
wild state, this can onty mean that it has, possibty as an improved 
race, been reintroduced into Ce 3 don from ]\Ialacca ; but, as the 
Alaha Pengiri is at the same time put down as the old or original 
citronella grass of Ceylon, it is more probable that the statement 
is due to some mistake. As to the Lenahaiu variety we haA^e 
more precise information. It originated about 1885 near Matura, 
in south Ccjdon, presumabty in a plantation, and in a short time 
almost entii’ely replaced the old grass, on account of its being so 
much hardier. Mells says of it : “It is in general appearance very 
lilce the Mdnd grass found on g)aianas up country.” 

(4) Cymhogjogon confertiflonis. — ^This grass is in all probability 
the parent plant of the citronella grasses. In Ce 3 don it is one of 


PE BP U 31 E B Y 

the nio=;t conspicuous elements of the vegetation of the palanasz 
Tn strong sunshine it emits an overpovering odour of citronclla. 
Tlie Cingalese name for it is 31dm, vliilst it is called Bamtc in the 
Nilgui vernacular. 

{;>) Cymhopogon jlcxuosns. — Tliis grass, formerh* known as 
Androp)ojon Jlcxvasm, Xces c.r Stcud., is known as Malabar or 
Cocliin grass, and is distributed in the Tinnivelli District and in 
Travancore, and during the past few years a large acreage has 
been planted with the grass. 

According to Stapf, Eheede, in his Hortus i\Ialabaricus,” 
described a grass under the name Kodi-pidlu, and its illustration 
is that of a grass very common tlu’oughout Travancore and the 
adjoining district of Tinnivelli. Bottler knew it, and put it down, 
though with some doubt, as Andropogon Nardns, which it resembles 
very much indeed. Ainslie (1813) mentions it as Stihlcanaroo- 
pilloo and “ gingergrass ” (the exact equivalent of the Tamil 
name), and says of it : “ This is a variety of the grass which is 
well known in Lower India by the name of the lemongrass ; it 
differs, however, from it in this respect, that, on being chewed, 
it has a strong flavour of ginger. It is very common on the 
Com'taUam Hi l l s in the Tinnivelli District, where the natives 
consider an infusion of it as stomachic and febrifuge.” And later 
on (182G) he adds : “ The natives occasional!}’- prepare with it 
an essential oil.” This, I believe, is the first record of oil being 
prepared from Malabar grass. IClein collected the grass in 1818 
on the same hiUs, and his specimens, which are also marked 

Snchinari gBlhi, Tam. ; gingergrass, Ang. ; Androp)ogon Nar- 
dus (?),” leave no doubt as to its identity vdth the plant from 
which the Travancore or Cocliin lemongrass oil is produced. 
Wight subsequently distidbuted specimens of the same grass as 
“ Andropogon ficxnosus, N.E.” It was not, however, described 
until 1855, when Steudel published a description, retaim’ng for 
it Nces’ name ; but not much notice was taken of Stcudel’s 
species, winch, if mentioned at all, was usually cited as a synonym 
ol- Andropogon Nardus, as, for instance, by Bentley and Trimcn, 
who, moreover, figured it as Andropogon Nardns. In 1889, Hackel 
distinguished it as a variety of the tj’pical Andropogon Nardns 
(citronclla grass), and the same jilace was given to it by Hooker 
in the “ Flora of British India,” but neither author coimccted 
it with the lemongrass oil of Travancore, which very generally 
was treated simplj- as “ lemongrass oil.” 

I\Iorphologically, C. flexnosus differs from the other species of 



t-lie Narchis series by its large, loose, greyish or slate-coloured 
panicles, the branches of which are particularly slender, long, 
flexuous, and often drooping, and by the less conspicuous spathes 
and the smaller, usually very slender and acute, spikelets. The 
basal leaf sheaths are rather narrower than those of G. Nardns 
and C. confertifiorns, and are not reddish within. 

When the Malabar grass oil — ^this name, 'svhich is used in 
Barber’s collection, is preferable to the name Travancore lemon- 
grass oil — ^v^as first exported cannot be decided precisely ; but the 
“ lemongi’ass oil ” mentioned by Pereira (ISoO) as imported into 
England from Cochin was very likely the oil of G. flexuosiis, and 
not of G. citrakis. In 1859, Major Heber Drury, vviting to 
D. Hanbimy and referring to a specimen of G. flexuosiis which he 
had sent him, says : “ Erom this species (and from this only) 
lemongrass oil is distilled in Travancore.” Eour years later 
Hanbury received the same plant from E. G. Waring, vdth this 
note : “ Andropogon (?), wliich yields the lemongrass of Travan- 
core — abundant on the plains — is not cultivated.” The statement 
in the “ Pharmacographia Indica,” vol. iii., 1893, p. 565, that 
the oil is distilled in Travancore from Anjengo northwards, and 
that the grass is burnt at the end of the ch’y weather, no doubt 
also refers to G. flexuosiis, and not to G, divaius, as the authors 
of that work believe. It is probably due to this confusion that 
Gildemeister and Hoffmann saj’’, quoting Dymock, Warden, and 
Hooper as their authorities, that “ the grass is ciiUivaied on a 
large scale onlj^ on the Malabar coast in Travancore, on the 
western slope of the mountains, north of Anjengo.” I\Ir. T. E. 
Bonrdillon writes quite recently from Quilon that only Avithin the 
last year or two extensive areas have been planted up with the 
Malabar grass. As the Travancore grass oil is not commercially 
distinguished from the oil of G. citraius, both being sold as 
lemongrass off, it is difficult to decide as to which oil pubhshed 
analyses refer. At all events, according to Stapf, the soluble East 
Indian lemongrass off is derived from this grass. 

(6) Gijmhopogon coloratiis. — ^This grass has a powerful lemon- 
grass odour, and is found from the TinniveUi District to the 
Anamallai Mountains, and also in the Madi’as Presidency. It 
may be sometimes mixed with G. flexuosiis for distillation 

Practically nothing is known of the conditions under which 
this grass grows ; but it has a distinctly xerophytic habit. It is 
a highly aromatic grass. There is, however, no evidence that it is 


P Eli F U M E BY 

used for extracting oil or for any otlier purposes, xinlcss it is one 
of the “ leniongi’asses *’ of the Slalabar district to wliich the 
following extract from the Madras Mail refers : “ The natives of 
Ernad and Waluvanad empirically distinguish no fewer than 
twenty-seven species of lemongrass, but say that only five of 
these varieties possess a commercial value. They also state that 
the most valuable of these varieties does not blossom. Ernad 
and Waluvanad, I am reliably informed, arc full of hills, on which 
lemongi'ass grows vild and could be had virtually for the collect- 
ing.” The variety which does not blossom is very jirobably 
C. ciiralus. 

(7) Cijmioj)ocf07i cilratiis . — Stapf is of opinion that this plant 
is that from which the lesser soluble lemongrass oils are distilled. 
Formerly known as Andropogon ciiraias, it is referred to by 
Samuel Bro^vne in his “Seventh Book of East Indian Plants” 
in the following terms : — 

“ Tliis is a most delicate sort of fragrant Gt'ass which being 
rubbed smells like Bainne and Lime or Limon peel together. The 
Portuguese Wo^nen fume their children -with it, and give the 
Decoction of it with other things for Fevers and to strengthen 
weak stomachs ; but the Natives use it not, which together with 
its gi’owing in Gardens on the Sea coast and not up the Countiy, 
as I can yet observe, makes me think the Portuguese brought 
this from other parts and planted it here ; certainly, so exceUeut 
a Plant of such Fragrant and Aromatik taste must have many 
Vert lies. I use it in many cases, and generally with success. While 
I was VTiting this, in came a Person, who saj’s, that about 30 3 ’-ears 
ago, viz., about 1G6G, one Antonio Palia, brought 3 Pots of tliis 
Grass from Batavia to Paliacut, one of which he sent to a Garden, 
here at Madrass.” 

The Portuguese in India termed it Herha cJieirosa, the equivalent 
of the Tamil Vasana-pnllu, and the Dutch named it Sereh, a name 
b.v which the grass is stiU ImovTi in Java. 

It is probable that the grass was inti’oduced into Cejdon during 
the Dutch occupation of the island. 

The comiiarativeh’- recent date of the cultivation of the lemon- 
gi'ass in India is evident from the nature of the established 
vernaculars. The Tamil Vasana-g^illu is merelj’’ the equivalent 
of the Portuguese Herha cJieirosa, under which name it was 
probablj” introduced. The term was taken up unchanged, or 
almost so, in Walavalim, Canarese, and Telegu. Another Tamil 
name, Karpfa-a-pulhi (camphor grass), is equall}' descriptive, and 



the same applies to the Gujerati and Marathi vernaculars, ■which 
mean “ green tea,” whilst the Dukni name given by AinsHej 
namely, Naring Ice has lea glians^ is a direct translation of “ lemon- 

The plant was sufficiently attractive in India to cause its early 
introduction into the colonies of, those European powers which 
had possessions in India. It was introduced into Jamaica at the 
end of the eighteenth centmy, and later into the Spanish and 
French colonies, and, probably through the Portuguese, into East 
Africa. In the Malay districts it is universally grown as a medicinal 
and kitchen herb. Its history there goes back, no doubt, far 
beyond the arrival of the first European invaders. We hear of 
it almost simultaneously from the Pliihppines and from Java as 
early as the first half of the seventeenth century. In 1635, Juan ~ 
Eusebius Nieremberg, a Spanish J esuit in the Philippines, describes 
it quite unmistakably under the name of Tanglat a term still 
in use for “ lemongrass ” in the Tagalog and Visayan dialects 
(spelt Tanglad). The passage, which is worth quoting, reads : 

“ Tanglat. It is a herb springing from a bulbous root, the swollen 
base of the leaf tufts, whitish-red vfithout, yellowish Tidthin ; 
from it rise 10-12 leaves, about 1 m. long, rather rough and 
moderately green ; there is, however, neither a (flowermg) stem 
nor fruit. The whole plant has a scent lilce that of lemon flowers, 
but stronger. Cooked, it improves the taste of stale boiled fish ; 
put into wine it gives a pleasant flavour, and it imparts a delicious 
odour to sauces and spices. The hquor distilled from it is almost 
scentless until exposed to the sun ; but this being done, it usually 
exhales a pleasant odour, and appfied to the face seems to sharpen 
and invigorate all senses and the head.” 

Stapf summarises the uncertainty of the origin of the grass as 
follows : — 

“ As the lemongrass is only known in the cultivated state, the 
question arises, what is its origin ? I am afraid it is yet too soon 
to give a satisfactory answer. It is true there is not, among the 
Malayan species of Cymhopogon, so far as I know them from the 
collections at Kew and the British Museum, a single one which 
suggests itself to my mind as the spontaneous state of the lemon- 
grass, and Bumphius’ statement that it occurs in the "wild state 
in Amboina is open to doubt ; but our knowledge of the Gymho- 
pogons of the Malayan region is still so imperfect that the possibility 
of the lemongrass having originated there is by no means excluded. 

“ The Oyrnhopogon most closely approaching C. citrakes that I 




linvc i? Cymhopogon pcnchiJus, Stapf {A-ndropoyon j^'-inhdus, 
Xi (.)■ Stciul.). collected by Wallicli in Xe2:)al. by Hooker. Kurz. 
and Clarke in the Sikkim Tcrai, and by C-iriiiith (No. G7G3) in 
‘ Bcngala.' Xo vernacular name i? given, there is no information 
concerning its j^roperties and uses, nor has it ever been connected 
with the lemongrass, and to do this, in the light of our present 
Icnowlcdge of the history of the latter, would involve a hypothesis 
bolder than I dare to advance. Another allied form, presumably 
from the same region, but less like lemongrass, and distinguished 
therefrom by less hairy racemes, borne on long common peduncles, 
which are frequently exserted from the sui^porting sheath, and b3'- 
smaller as relatively much broader sj^ikelets, was figured as 
‘ Avdropogon ScJKxnrtntJnis ' (qua ‘ lemongrass ’) by "Wallich. and 
referred to Andropogon Nardus, var. cxscrtiis, b3'’ Hooker. It was 
in cultivation in the Calcutta Botanic Garden, and maj’^ have 
been raised from the seeds of a fairly distinct Androqwgon of the 
Nardus series, wliicli extends from the Saharanpur Terai to the 
Garo Hills, and possesses ver3’' aromatic citron-scented leaves. 
However this may be, neither Wallich’s plant nor its presumably 
wild representative agrees sufRcientl3’ with the lemongi-ass to 
suggest the derivation of the latter from either of these species.” 

(8) Cymhopogon Martini . — This grass is the plant from which 
palmarosa and gingergrass oils are obtained. The differences 
between the two oils are so pronounced that some marked 
difference between the distillation materials must e.xist. It has 
been suggested that the period of growth at which the grass is 
cut is responsible for the difference in the oils. But this is highl3’- 
imiorobablc, and it seems certain that there are two varieties of 
the gi-ass, whoso morphological differences are not 3'et settled. 
The following account of the foundation of the .species is given 
b3' Stapf, the grass having been originalh' named Androjiogon 
Martini. It is known in India to-da3’- as Rusa or Rosha grass : — 

During the Avar of 1790-1792 against Tipu Sultan, Claude 
Jlartin, aa'Iio joined the expedition in 1791 as a Commissioner of 
provisions and aide-de-camp to Lord CoriiAvallis, collected “ in the 
highlands of Ballaghat ” the seeds of a grass Avhich had struck 
him, owing to its excellence, as a fodder plant, as avcII as on 
account of its pungent taste and aromatic odour, aaIucIi Avas so 
strong as to impart itself to the milk of the coavs which fed on it. 
From the seeds he raised an abundant crop at LucknoAv. He al.^o 
supplied Roxburgh “ AA'itli a small stalk, roots and seed.” The 
“ small stalk ” is not preserved ; but Roxburgh grcAv the grncs 



from tlie seed iii the Calcutta Botanic Garden, and of the specimens 
thus raised there are two at the British Museum, one from Eox- 
hurgh’s herbarium, the other from General Hardmcke’s collection. 
The first is named “ Andropogon Martini ” in Roxburgh’s own 
hand ; the other, under the same name, bears the date Feb- 
ruary 18th, 1789. The name did not appear in print until 1814, 
whilst the description, although efficiently written before 1799, 
was only published in 1820. 

Dr. Maxwell, Assistant Surgeon at Asirgarh Fort, in Nimar, 
wrote, in 1824, a letter to the Medical Board of the East India 
Company, in which he called attention to a fi-agrant grass which 
was “ found in great abundance On the sides of the liill fort, as 
well as all over Malwah. From it,” he says, “is extracted a 
highly pungent essential oil (when in its pure state), which I can 
from experience confidently recommend as of the highest benefit, 
when applied by friction, in rheumatic affections,” and, further, 
that “ it is prepared by a very rude process under Jaum Ghaut, 
hi the vicinity of the station of Mundlaish’.” ■ The specimens 
which he sent with his letter were submitted to Wallich, who, in 
his reply to the Medical Board, reported as stated above, adding 
that he himself had found the plant abundant in Nepal. In the 
following year, J. Forsjfili, who had been directed to investigate 
the matter on the spot, presented a paper to the Medical and 
Physical Society of Calcutta, in which he gives a detailed account 
of the preparation and the sale of the oil and the conditions under 
which the grass grew and was gathered. He also gives Roosa-lca- 
Tel as the native name of the oil. Of the grass, he reports that 
it “ is met vfith in frequent distinct patches in the jungle tlu’ough- 
out the province of Nemaur, but in greatest abundance along the 
foot of the Vindliya Range, near Nalcha, at wdiich two places 
only, I believe, it is prepared, at least' to any amount. About 
the latter end of August it begins to bud, and continues to flower 
in tolerable vigour till the end of October, d-uring which period 
alone it gives out the oil in’sufficient quantity to cover the expense 
and trouble of its preparation, as after this it speedily dries up, 
and what httle oil it does yield is extremely acrid, and unfit for 
use. . . . The oil is obtained from the grass by distillation . . '. 
the plant is cut across where it begins to give o.ut its flower, and 
bound up into small bundles. . . .” A few years later (in 1830), 
Charles Hatchett, F.R.S., a prominent chemist, received a sample 
of oil from a Mr. Samuel S'winton, who had been in the East India 
Company’s service for many years and had resided for some time 


PEliF U 21 E R Y 

in Mnlwa. Hatched made the grass ■ndiich ^dclclcd this oil the 
subject of a somewhat confused paper, entitled “ Spikenard of 
the Ancients ” (183G). Swinton, like iMaxwcll, first became 
aerpTainted with the oil (wliich lie says is called JRhoJiscc-kc-Tell 
by the natives) as an effective remedy in severe attacks of 
rheumatism. He also stated “ that althoxigh the jfiants are found 
in other parts of India as well as in Malvah, j^et those which 
grow about the Jaum Ghaut arc preferred, and gathered in the 
month of October, when the seeds forming the ears or spUces have 
become fully ripe. At that season, however, in the places where 
this gigantic grass is x^roduced, the jungle fever is so prevalent 
that the peasantry who collect it will not ex^Dose their health . . . 
unless tempted b}’’ very high remuneration. . . Hatchett 
further adds : “ Mr. Swinton was informed by them (the prmcipal 
natives) that it has been prepared in and about Malvah from 
time immemorial, at first probably by the Parsees, although at 
present it is entirety in the hands of the Borahs, a very com- 
mercial people, forming a sect of jNIoslems, whose cliief resides at 
Siu’at. The oil is obtained fi’om the spikes, which, when ripe, 
are cut until a portion of the stem about 1 foot in length, and 
are then subjected to distillation. Only a small comparative 
quantity of the oil is consumed by the natives, the greater part 
being now, as was the case in very remote times (according to 
tradition), sent as an article of commerce to Arabia.” Finally, 
it is stated that “ the odour of the plant is so powerful that, 
although camels unll cat almost any vegetable, yet they will not 
browse on this. . . Neither the production nor the export of 
the oil can, however, have reached any considerable dimensions, 
as jacquemont, who, in the spring of 1832, visited Nalcha and 
Jaum, and gave a very full account of Slalwa, does not mention 
the grass or the oil. The grass, it is true, might have escaped 
him, as at that season it must have all been dried up. 

How far there is any truth in the tradition that oil has been 
distilled from the Rusd grass “ from time immemorial ” we do not 
know. The authors of the “ Pharmacographia Indica ” (vol. iii., 
p. 558) merely suggest that “ the industry commenced in the 
eighteenth centurj*, wlulst Kliandeish was in a flourishing con- 
dition unders its Mahometan rulers.” However this ma}’- Ijc, 
there is sufficient evidence that the grass must have been known 
to the Aryan j)Coplcs of India for a very long time. Rohishcr, 
the Sanskrit equivalent of the Hindi Ritsd, occurs in “Susruta ” 
and in some of the earliest Sanskrit dictionaries. Another name 



in Sanskrit, evidently from the same root, is' Rdseni. Variants 
of these terms are generally recognised vernacular names in the 
Hindi, Gujerati, and Mahrati dialects. Curiously enough, the 
name does not appear in the earher Persian pharmacopoeias, the 
first record of it, Rus, being apparently in the “ Makhzan-el- 
Adwiyaii ” (1771). According to the authors of the “ Pharmaco- 
graphia ” (vol. iii., p. 557), C. Martini is also “ the Bhustrina or 
Blmtrina (‘ earth grass ’) of the Raja Highanta,” and among the 
synonyms which it hears we may mention Gandha-Kheda and 
Gandha-trina (“ odorous grass ”), 8u-rasa (“ well-flavoured ”), and 
Su-gandlia {“ having an agreeable odour ”). 

(9) Cymbopogon ccesius. — ^This grass, formerly known as Andro- 
pogon ccesius, or Kamakshi grass in Tanul, very closely resembles 
the -Rusd gi’ass or geranium grass used for distilling palmarosa 
oil. In the Carnatic the Rusd grass is replaced by a closely alhed 
form vdth more slender and more branched culms, usually from 
|- to 1 metre high, vith narrower, thioner, often almost flaccid 
and very glaucous leaves, and vith generally smaller panicles, 
which seem to retain their glaucous colour, or merely turn straw 
colour when mature. The structure of the spikelets is, however, 
that of G. Martini, and so closely does the Carnatic grass in some 
instances approach the narrow-leafed state of’ G. Martini that 
there would be no difficulty in constructing a chain of intermediate 
stages, linldng together both forms as completely as possible. 
Those transition forms are, however, so far as I can see, confined 
to the border districts where the two grasses meet ; elsewhere 
they are sufficiently distinct. 

The oldest specimens of the Carnatic grass on record are a 
specimen in the Plul^enet herbarium at the British Museum, and 
several in the Du Bois herbarium at Oxford, aU of them collected 
near Madras at the end of the seventeenth or in the early years 
of the eighteenth century ; but it is very probable that a passage 
in a letter by Herbert de Jager to Rumphius, dated July 6th, 
1683, also refers to it. Contesting the view of Bontius and others 
that the Sereh of the Malays is identical with the Scho&nantUim 
of the herbalists, and, in support of his argument, he says : “ I 
have become famfliar with the true and genuine SchcenantJmm 
in Persia, and particularly on the coast of Coromandel, where I 
have traversed whole fields of that grass, which is about 2|- to 
3 feet high, and the scent of which may be noticed from afar, 
particularly during the night, 'when dew falls, or in day-time 
when it rains, whilst in sunsliine and fine weather not much 



O'lnnr i< perceptible. In Golconcla this Scho:nanOium ground into 
pcnvder is u.^ccl for washing the hands on account of the sweet 
scent it imparts to the water ; though the odour docs not persist 
vchen the Iiands get diy."’ Neglecting for the present the question 
as to wliat the SclKxnantlmin powder of Golconda was, there 
can be little doubt tliat the fragrant Coromandel grass, of wliich 
there veere whole fields to traverse, was the Kdmdtci-])ilhi of the 
Tamils. Of this name wo hear for the first time in Samuel 
Browne's “ Seventh Book of East Indian Plants,” edited and 
commented on by Petiver (1702). The plants which form the 
subject of the paper were collected “ between the 15th and 20th 
June, A.D. 1G96, in the ways between Fort St. George and 
Tripjjetcc, wliich is about 70 miles oS.” One of them was 
ComacJiee inllee, and of it Browne saj’^s : “ This is Schoenanth, 
which the natives here have not in great Esteem,; sometimes in 
the i\Ioors’ Camps, the Horses, Camels, and Oxen which cany 
biurthens eat nothing else ; it is generally 2 or 3 feet high here 
about (but near Color in reech sojd, I have seen it 8 feet high) 
[tliis gigantic grass is no doubt C. Mariini] and thick as a Quill 
or small Reed ; It’s sometimes by the natives put into their 
Decoctions for Fevers, and ivitli us is deservedl3>' of more esteem.” 
Petiver identified the Comach-ee pillea with Plukenet’s Gramm 
Daciylon Maderas], figured on Plate 119, Pig, 2 of his 
“ Almagesta ” (1691), the type of which is in Plukenet’s herbarium 
— ^it is the specimen referred to above. 

C. ccEsius seems to inliabit the greater part of the Carnatic, 
from the extreme south to the Chingalpat District. It is evidently 
common,- on the whole, in that region, but little use seems to have 
been made of it so far, except as an occasional domestic remed3^ 
There is, however, among the specimens communicated bj’- JB. 
Barber, one with a note to the effect that it is the “ grass from 
which Jlr. Proudlock has been distilling oil.” A short account 
referrmg to it is contained in the “ Administration Report of the 
Government Botanic Gardens and Parks, the Nilgiris,” for 1901, 
p. 0. According to this report, the grass was obtained from Arni, 
in the North Arcot District, where it is stated to grow in great 
abimdanco. The yield of oil from a freshly cut sample received 
at the end of December w'as 0-431 per cent. Another and larger 
quantity, wliich was received in April in a thoroughlj^ dri’- con- 
dition, jnelded 0-711 per cent, of oil, the differences in the jdcld 
being attributed to the first lot being fresh, whilst the other was 



(10) Gynihopogon polyneuros. — Just ^as C. Martini is replaced 
in the south-east of the Deccan Peninsula by G. coesius, so 
another species takes its place in the south-west. This species, 
G. jiolyn&uros, is, however, much better defined than G. ccBsius, 
It is a moderately robust grass with a tendency to copious branch- 
ing from the collar so as to form dense tufts of culms, with 
somewhat persistent narrow basal sheaths, rather fat, smooth 
blades with a rounded base, more or less glaucous beneath, and 
often suffused with pm’ple along the margin, and with short, 
contracted variegated panicles, the herbaceous sheaths being 
usually deep brown-green with a narrow scarious • margin, the 
spikelets being green in the lower part, and more or less blackish- 
purple in the upper. It was first distributed by Wight (No. 1705) 
under the name A-ndropogon versicolor, N.B., a name chosen, no 
doubt, in allusion to the variegation of the inflorescence. Nees 
never pubhshed a description of it. On the other hand, Steudel 
has, in his “ Synopsis Plantarum Graminearum ” (1855), p. 388, 
an “ Andropogon versicolor , Nees MSS.,” under which he c|uotes 
“ A. Schoenanihus , Wall. Cat. n. 8794L.” Wallich’s Cat. n. 
8794L.” is in Wallich’s ovm herbarium identical with n. 8794K., 
which Steudel [loc. cit.) cites under Andropogon clandestinus, Nees. 
Steudel’s description of Andropogon versicolor agrees neither vnth 
Wight’s No. 1705, issued as ” Andropogon versicolor, N.E.,” nor 
vdth Wallich’s n. 8794L. It is mot clear what the plant which 
Steudel had in mind was ; it cannot well have been Wight’s 
Andropogon versicolor, N.E.’- Wight does not indicate the 
locality where his No. 1705 was collected beyond the general note 
“ Peninsula Ind. Orientahs.” It agrees absolutely, however, with 
a grass which ha's freq^uently been collected in the Nilgiris, among 
others by Hohenacker, who distributed it as 933, Andropogon 
{Gymbopogon) nardoides )3 minor N. ah E.” ; this was made by- 
Steudel the type of his Andropogon polyneuros. That name being 
perfectly unambiguous, its specific component wiU have to be 
i-etained for the NUgiri grass hi question in preference to versicolor, 
although the latter has very generally been applied to it. Outside 
the Nilgiris, G. polyneuros has so far only been observed in 
Ceylon, where it is, particularly at higher elevations (up to 1,500 
metres), a locally common plant. Thwaites has already called 
attention to the ” rather agreeable aromatic odour of the 
inflorescences of this species, adding that . the essential oil 
appears to be situated principally at the base. of the spikelets. 
According to a note in the Tropical Agriculturist for 1901 

304 = 


(p. 873), the odour of the crushed leaves resembles that of fennel 
or anise. 

(11) Vcimria zizanioidcs is the cus-exts or Uim-hlias grass, from 
'vvluch vetivert oil is produced. It 'was former]}^ knov-ii as Amlro- 
pogon mvrkatus. In the vdld state it is distributod over most of 
British India and Ceylon, being found on the banks of rivers and 
on rich marsliy soil up to an elevation of l.SOO feet. It is some- 
times cultivated, as, for example, in Rajputana and Chutia- 
Nagpur. It is cultivated in the I^Ialay districts, the West Indies, 
Brazil, and Reunion. 

The Hindu name for the grass is J:Jias-kJias^ the name vetivert 
being of Tamil origin. Jones in 1795 identified the Ueiva of 
Kalidasa with and Hessler did the same in his transla- 

tion of the Ajmrvedas.” 

The natural area of this grass in India and Ceylon includes 
practicaU 3 ^ the whole countrj^ in the north up to altitudes of 
GOO metres. Although common in many' parts of the country, 
particularly on the banlis of rivers and in rich marshy soil, it is 
also at present, as in Rheede’s time, occasionally cultivated, as, 
for instance, in Rajputana and in Chutia-Nagpur, Eastwards the 
area extends into Burma, Tluoughout the Llalayan region, how- 
ever, it ocem’s only in the cultivated state or as an escape from 
gardens. It has also been introduced into the Mascarenes, the 
West Indies, and Brazil ; but it seems that in these countries oil 
is not distilled to any’' appreciable extent, except perhaps in 
Reunion, where the gi’ass must have been in cultivation for at 
least 100 years, -as the first sample of vetivert oil that was 
chemically’' examined (in 1809) came from there. (See also under 

Vetivert Oil/') 

(12) Andropogon odorahis. — ^Tliis grass, knoum in India as 
XJsadhana^ is a little-known grass which was discovered by^ 
Dymiock at Thana in 1875, and mentioned on account of its 
strong odour of ginger under its vernacular name, Usadliana, in 
the first edition of his “ Materia Medica of Western India ” (p. G93). 
In the second edition of that work (p. 853) it was referred to 
Andropogon Mardiis. Subsequently it was, however, recognised 
as a new species by- Sirs. J. C. Lisboa, and described as A. odoraliis. 
This very aromatic grass is used by the peasantry of the Tliana 
District for medicinal purposes. An essential oil of a golden-yellow 
to a deep sherry^ colour, vith a distinctive odour, was obtained 
from it by^ distillation, but it lias not y^et become an article of 
commerce. The odour is, according to the “ Pharmacograi)hia 




Indica,” vol. iii., p. 570, at first that of cassia and rosemary, but 
afterwards that of oil of cassia or, according to Gildemeister and 
Hoffmann, that of pine-needle oil. 

GRIFFES DE GIROFLE. — ^The flower stalks of the cloves, 
separated whilst they are dr^dng, are knovm in Zanzibar as 
Vihunia, and in France as Griffes de Girojle. 

GUAIACUM WOOD OIL. — See “ Bulncsia Sarmienti, Oil 
of,” and “ Champacol.” 

GUAIOL. — ^Although this body has not any odour value, 
it is of interest as being the only well-identified constituent of the 
so-called guaiacum wood oil — ^the oil of Bulncsia sarniie 7 iti. It is 
a sesquiterpene alcohol, of the formula CigHocO, melting at 91°, 

20 ° 

of specific gravity 0*9714 at — , and having a refractive index 

1*5100 at 20°, and specific rotation about — 27°. (See also 
Gandurin, Berichic, 41, 4359). 

GUM THUS.— See “ Boswellia Resin.” 

GURJUN BALSAM OIL. — Gurjun balsam is an oleoresin 
derived from various species of Dqoterocarpu^. It is a viscous 
substancccloscl}' resembling balsam of copaiba in general charac- 
ters, and is used to some extent as an adulterant of copaiba. 
It has no direct relationship with legitimate perfumery, but is 
found as an adulterant of manj’- essential oils. The oleoresin, on 
distillation, yields about 50 to 60 per cent, of an essential oil, 
having a specific gravity 0*915 to 0*935 ; optical rotation, — 30° 
to — 135° ; refractive index, about 1*5050 ; acid value, 0 to 1 ; 
and ester value, 4 to 8. 

Gurjun oil is a colourless liquid of sharp odour, but of no value 
as a perfume material. It is, however, of interest on account of 
the fact that it has been used to a considerable extent as an 
adulterant of Indian palmarosa oil. It is easity detected by 
analysis in this oil ; and as palmarosa oil is used as a raw material 
for the production of geraniol, traces of the adulterating gurjun 
oil remain in the geraniol produced from the palmarosa oil. 
Geraniol so produced is used to some extent as an adulterant of 
otto of rose, and if the adulterating geraniol has, in fact, been 
manufactured from palmarosa oil already adulterated with 
gurjun balsam oil, traces of the adulterant are easy to detect in 
the otto of rose. Gurjun oil, or any oil containing more than traces 
of it, gives the following characterisic colour reaction, wliich is a 
practically definite proof of the presence of the oil as an adul- 



tcrani. If 5 to 10 drops of the suspected oil- are added to a 
luixlure of 10 c.c. of glacial acetic acid containing about 5 drops 
of nitric acid, a violet colouration -vrill result almost immediatel 5 ^ 
If no colour results vithin one minute, it maj" be taken for granted 
that this adulterant is absent. This oil has no interest to per- 
fumers other than as an adulterant, as above indicated. 

HARDWIGKIA BALSAM. — ^The so-called African copaiba 
is of no interest to the perfumer, e.vcept that the essential oil 
distilled from it is from time to time used as an adulterant of 
perfumery oils. There is considerable doubt as to the botanical 
origin of the balsam. It is usuall}- ascribed to Ilardiuiclda Mannii. 
It has also been said to be the product of Oxystigma Mannii, and 
it has recently been suggested that it is derived from Daniclla 
iliurijcra. It is a thick, viscid oleoresin, containing about 40 to 
53 per cent, of essential oil. The characters of the balsam are as 
follows : specific gravity, 0'985 to 0-998 ; acid value, 53 to G5 ; 
ester value, G to 10. It is also known as iUnrin balsam. The 
essential oil is a colourless liquid having the following characters : — 

Specific gravity . . . 0-915-0-932 

Optical rotation . . . -{- 5° to -f- 37° 

Refractive index . . . '1-5000-1-50CO 

Acid value .... 5-10 

Ester value .... 0-G 

Ester value after acetjdation . Up to 12 

It does not yield any characteristic colour reactions b 3 ' which 
it can bo detected, as does the similar gurjun balsam oil, so that 
the best method for its detection lies in a careful comparison of 
the ph^'sical characters of the various fractions of a genuine and 
a su-si^octed oil. A pure African copaiba oil, distilled bj- the 
writer (E. J. P.) and C. T. Bennett, jiclded the following four 
equal fractions of 25 per cent, each, on distillation : — 

Specific gravity. 



Refractive index. 



1 1 

-f 17° 30' 



3 1 

-b 4G° 

4 ! 

• -{-55° 

Similar results were found with other normal samples of 
African copaiba oil. Oil of peppermint has been found by the 

307 CO-2 

P E PEI' :!/ E P y 

writer grossly adulterated with this oil. The influence of the 
adulterant is cleai-ly indicated in the fractionation of the oil, by 
the entirely abnormal increase in s])ccifio gravity, oj)tical rotation 
to the right, and j-efraetive index (jf the laler fractions of the 

HAWTHORN PERFUME.-'.rhe basic material used for 
the manufacture of fdl hawthorn ])crfumes is arliticial hawthorn, 
usually known as aubejjine {ride "Anisic Aldehyde’’), ^^‘lrious 
lloi-al extracts are based u])on this to round it off and give it a 
distinctive odour, according to the individual })crfumer's taste. 
The natural ])crfume of mayblossom, Crdlrrgur o.ri/rdiithn, is not a 
commercial article. 

HEDYOSMUM.— The so-called tobacco of Jamaica is 
llrdi/osminn uuUnis. .Tt yields an essential oil which recalls the 
odour of certain tobaccos, .and is said to be of value as a soap 
perfume. It has so far. however, not i!])])cai-(-d on the marked as 
a commercial article. 

HELICHRVSUM OILS.— Various species of heliehry,-um, 
a genus belonging to the natural order Co)i>posila\ yield essential 
oils having an odour value, lldichru.snm f-'dralilc. according to 
1‘Tanccsconi and Sernagiotto {Gazz. Chin}. -14, 1!114, ii., 410). 
yields an oil with an odour recalling that of roses, and having a 
s])ccilic gravity 0-tK)2 ; o]itieal rotation. — ll-?” ; and refractive 
index, 1-47G0. Its constituents are unknown. 

lldichrijsnm arcnariinn yields 0-4 per cent, of essential oil of 
powerful aromatic odour recalling that of celery. Its specific 
gravity is 0-021 at 20° ; acid value. M-.a ; and ester value, 0. It 
probably contains paro-cresol. Jlclit'hri/.sum angn-'^tifolium is a 
fragrant herb widely distributed in southern Europe. It grows 
in masses near (tenoa, and also in Hungary and Dalmatia. 
Echinimcl Co. {Pc.porL October, 1002. 72 : A])ril, 1000. .77 ; 
Api'il, 1014, 0.7) obtained from it 0-07;7 jier cent, of essential 
oil of specific gravity 0-802 to 0-020 ; optical rotation, + -1° 25' 
to — 0° 40'; refractive index, 1-4745 to 1-4S40 ; acid number 
up to 15 ; and ester value, 20 to 124. The oil is rich in nerol, 
partly in the free state and partly in the form of esters. 

HELIOTROPIN. — The perfume of heliotrope, commonly 
known as " cherry pie,” Avas for many years a great favourite, 
although it has probably lost its popularity owing to its having 
been overdone by aii indiscreet use of the artificial hcliotropin to 
excess, with the result that inany perfumes containing it arc so 


PERFV ME li 1' 

ptrong as to be vulgar and objectionable. Tlie orcbnar}- heliotrope 
plant is a native of Peru, lldiolropiim. Pcnivianuin, belonging to 
the natural order Boraginaccce. This plant vas introduced into 
Europe about the middle of the eighteenth century. There are 
a very large number of .“jpecies of the genus, which are for the 
most part highly odorous, and which arc found distributed all 
over the world, especially in tropical and sub-tropical regions. 
The flowers are treated to a small extent for the natural perfume, 
and the triple extract, absolute and concrete, are obtainable on 
the market. The bulk of the hehotrope perfumes sold to the 
public, however, are cither entirely or chiefly based on the 
artificial heliotropin. This body very faithfull}' reproduces the 
odour of the jdant, but is rather too crude, and requires “ rounding 
off.” This is best acHeved by the use of a verj' small amount of 
vanillin, together with a very minute quantity of benzaldehyde. 
Numerous other bodies blend well vdth hcliotropin, but where 
used to anj^ extent, result, of course, in a fanc}'’ perfume in which, 
pro tanlo, the heliotropin has lost its characteristic dominating 

It was in 1876 that Tiemann and Haarmann, m the course of 
their researches on the perfume of this plant, recognised that it 
was in the main due to two bodies, heliotropin and vanillin. 
Various types of vanilla beans, and also the flower of the meadow- 
sweet {Spircca Uhnaria), were also found to contain very small 
quantities of heliotropin. In 1910 Elze found it to be present in 
the essential oil of Pohinia psemlacacia, and soon afterwards 
Dieterich claimed to have detected traces of it m ordinary’- bees- 
wax. Its occurrence in nature, however, is rare, and wherever 
it is found it exists in very small quantity, usually in minute traces. 
It is probably formed in the plant by the decomposition of a 

To-day the world’s supply of hcliotropin is derived from oil of 
camphor, which contains a large quantity of safrol, the raw 
material which jdelds heliotropin. Originalty, however, artificial 
hcliotropin was made from the alkaloid piperine C'l^HjyNOa. 
Pejiper (preferably Singapore pepper), which contains from 7 to 
9 per cent, of the alkaloid piperine, is ground to a fine powder and 
mixed with twice its weight of slaked lime and a little water, and 
the mixture evaporated to drTOCSS. The dry mass is then 
extracted \nth ether, which dissolves the alkaloid, which is left 
behind on the evaporation of the solvent. The piperine is then 
boiled for some time with alcoholic potash,' In* which means it 



is converted into potassinm piperate’. Tins body is dissolved in 
fifty times its weight of water, and is then oxidised by means of 
potassium permanganate. The manganese oxide formed is filtered 
ofi and the filtrate evaporated, when the heliotropin crystallises 

Safrol {q.v.) is the odorous constituent of oil of sassafras, but it 
also exists to a considerable extent in camphor oil, from wliich it 
can be obtained considerably cheaper than it can from sassafras 
oil. In 1890 Eyckmann found that safrol yielded heliotropin, or 
piperonal as it was then frequently termed, on oxidation. It was 
also found that the yield was better if isosafrol were used. 
Ciamician and Silber {Berichte, 1890, 23, 1160) found that, if 
potassium permanganate were used for oxidation, a ketonic 
derivative was formed which diminished the yield of heliotropin, 
but that, if biclnomate of potash were used, this did not 

In the commercial production of heliotropin camphor oil is 
fractionally distilled on a very large scale, and the safrol so 
obtained is heated with alcoholic potash, and is thus isomerised to 
isosafrol in the same way as eugenol is isomerised to isoeugenol 
for vanillin manufacture. The isosafrol is rectified, and is then' 
oxidised as follows : A mixtm’e of 25 parts of bichromate of 
potash, 80 parts of water, and 6 parts of sulphuric acid is poured 
slowly into 5 parts of isosafrol with continual stirring, the tempera- 
tm’e not being allowed to rise materiallj^-. When the reaction is 
complete, the reaction mass is steam distilled and the distillate 
is extracted with ether. On evaporation of the ether, the helio- 
tropin, in an impure condition, is left behind, and is pm’ified by 
conversion into its sodium bisulphite compound in the usual' 

Several patents have been taken out for the manufacture of 
heliotropin by oxidation of isosafrol by means of ozone (, British 
Patent No. 6593 of 1895). There the oxidising agent is ozonised 
oxygen, which oxidises the isosafrol, preferably dissolved in acetic 
acid. When the oxidation is complete, the acetic acid is evaporated 
in vacuo and the heliotropin extracted with ether and purified 
by means of its bisulphite compound in the usual manner. 
Heliotropin can also be made by treating protocatechuic aldehyde 
with methylene iodide in the presence of an alkali. This method, 
however, is not a commercial one, but has confirmed the constitu- 
tion of the compound. 

•Heliotropin is a white crystalline compound melting at 37°, 


PEEEV M E i? r 

Its perfume is po'u-erful and very sweet. It is, Iiowercr, injuriously 
affected by. exposure to a temperature several degrees below its 
melting jmint, and it shoiild therefore be stored in a cool place. 
It is also better to keep it in a dark place, as the effect of strong 
light appears to be adverse to the keeping properties of heliotropin. 
Some perfumers always keep heliotropin dissolved in alcohol, 
ready for use as required, when decomposition is largel 3 ^ obviated. 
There arc many fanc}' names resemblhig hehotropin, but most 
of them mereh- disguise a mixtm'e of pure heliotropin with a little 
vanillin or coumarhi, and a fanej* price is paid for them. The 
intelligent perfumer will purchase pure heliotropm and do his o%vn 
blending. The determination of the melting point is the best 
criterion of the purity of this substance. This should be sharp 
at 37° to 38°, a gradual melting indicatmg adulteration. If an 
exhaustive examination is required, hehotropin may bo converted, 
bj’- excess of bromine in carbon bisulphide, into bromopiperonal 
CcHoBr.(CH 0 )( 02 .CIIo), winch forms ciystalline needles melting 
at 129°. It also forms two isomeric oximes, of which one melts 
at 110 ° to 112 °, and the other at 146°. It jdelds a semicarbazone 
melting at 146°, and a nitro-derivative melting at 94° to 95°. 

HELIOTROPYL-ACETONE.— This body, or piperonsd- 
acetone, is a crystalline compound melting at 55°, and boiling at 
165° at 12 mm. jmessure. It has a characteristic and yerj’- pleasant 
floral odour. According to Kaufmann and Radoscvic {BcricJdc, 
1916, 59, 675) it can be prepared by emulsif^dng an acetone 
solution of heliotropin with water and treating the emulsion with a 
40 jocr cent, solution of caustic soda. This results in the formation 
of pipcronal-acctone melting at 107° to 108°. Hj'drogen in the 
presence of colloidal palladium reduces this to pipcronjd-acetone. 

HEMEROGALLIS FLAVA. — ^This plant is knovm as the 
j'cUow Its natural perfume is not obtainable, but an 
artificial perfume is sometimes made bj’- using terpineol, hych’oxj'- 
citroneUal, am 3 d sahc 3 date, and similar synthetics. It is not, of 
cornse, more than a rough cop 3 ’' of the natural perfume. 

HEPTANE. — ^This bod 3 * is one of the alij)hatic or fatty h 3 'dro- 
carbons which arc of rare occurrence in essential oils. It is a 
vcr 3 - volatile liquid of the formula C 7 II 15 , of specific gravity 0 - 688 , 
and boiling point 98° to 99°. It has been foimd in the essential oils 
of Pinits Sal{nia7ia, Pintis Jeffreyi, and a few other allied species. 


, 311 


the parent substance of a new and most important series of 
artificial perfume materials. Of these amyl-heptine carbonate has 
ah’cady been described. It mil here be convenient to deal with 
tlie heptine carbonates together with allied acetylenic esters. 
The chemistry of this important group of bodies is w^ell sum- 
marised b}’’ Valli-Donan {American Perfumer, 1923, 133, and Rev. 
de la Parfximerie, March, 1923, p. 4). He points out that among 
the constantly increasing number of organic synthetic products 
wiiicli have been found useful in perfumeiy, methyl heptine 
carbonate deserves a special place, on account of the unusual 
interest of its method of manufacture, as Avell as the remarkable 
advantages of its use. 

The preparation of this ester requires the most painstaking 
technique and delicate management at the disposal of modern 
chemistiy. Nevertheless, its development from the laboratoiy 
to the factoiy scale has been effected -without mishap, the industrial 
product attaining, from the start, a high degree of perfection. 

It was in the course of the research of kloureu and Delange 
{Bull. Soc. Gliim., 1903, 29, 648) that method heptine carbonate 
was discovered, together with numerous other derivatives ha-\dng 
the triple bond. 

Metlyd heptine carbonate 

CH 3 .(CH 2 ) 4 .C : C.CO 0 CH 3 

is a colourless hquid, mobile, boihng at 107° at 20 mm. pressure, 
and having a specific gravity 0-9524. When pure, it has a strong, 
sharp, penetrating, disagreeable odour. But wdien sufficiently 
diluted, it gives off a very fine and very persistent fragrance of 
fresh violets, which renders it very valuable m the compoundhig 
of extracts and original perfume compositions. 

In conjunction with the ionones and metlyl ionones, it is 
capable, in some measure, of replacing violet extracts, and of 
imparting an original note to the perfume bases, more and more 
complex, used by the perfumer. 

If one considers a true acetylenic hydi’ocarbon of the general 

R.C : CH, 

it is clear that the end hydrogen atom, the one which is attached 
to the carbon atom bearing the triple bond, possesses acid 
properties, and that it is therefore possible to replace it b 3 ^ a 
monovalent metal, for example, sodium : 

R.C i CNa. 



The Forlium h>tlrocarbon corai^ound thus formed is a molecule 
capable of many reactions, and, in particular, reacting especially 
easily v/itli halogen derivatives. 

If it is treated vith a chlorocarbonic ester, there will be formed 
directly an acetjdenic ester : 

E.C i eXa Cl.COoRi = XaCl + RC i C.CO„Ri 
R and R^ may be identical or different, aliphatic or cyclic. 

In the case of methyl hci^tine carbonate the equation becomes 
CH3.(CH-.),.CiCXa + ChCOoCH^ = 

CH3.(CH2).j.C : C.CO0CH3. 

The order of procedure is therefore : — 

(1) The preparation of an acetylenic hydi’ocarbon. 

(2) The making of its sodium derivative. 

(3) The subjection of this sodium derivative to the action of a 
chlorocarbonic ester. 

In the preparation of meth}'! heptino carbonate the starting 
material is the ricinoleic acid existing in castor oil. When heated, 
this acid gives an aldehyde containmg seven carbon atoms, that 
is, cenanthol, also called heptanal, which is then to be chlorinated 
bj’ means of phosphorus pentachloi’ide. 

The resulting dichloride, saponified with potassium hydroxide, 
gives heptine. 

It is possible to represent tliis series of reactions b}’’ the following 
equations : — 

(A) Castor oil — > CigHgjOg -> CigHigGOoH (by-product) 

Pvicinoleic acid Undocylenic acid 


(B) CH3.(CH„)5.C0H -f PCI3 


(C) CH3.(CH2)5.CHCl2 



(D) CH3.(CH2),.C:CH 


(E) CH3.{CHo).,.C:CNa 

Heptine Fodiuni 

(F) CH3.(CH3),.C ; C.CO0CH3 

Hclhyl heptine carbonate 

A. Preparation of Ilcpfanol 




Tlie decomposition of ricinoleic acid is effected by heating crude 
castor oil (Kraft, Bericliie, 10, 2034 ; Erlenmeyer, Annalen, 176, 
342 ; Jourdan, Annalen^ 200, 1020) in a distilling apparatus of 
enamelled iron, using direct heat at 160° to 170° under a pressure 
of 100 mm. 

The heptanal, -which distils off together with a small proportion 
of water, is fractionated under a pressure of 9 mm. The distilling 
apparatus should be capacious, for there is considerable foaming. 

The yield from tliis operation is quite small (10 to 12 per cent.), 
and part of the undecjdenic acid becomes polymerised. Haller 
has suggested that the decomposition be performed not upon 
ricinoleic acid, but upon its esters. 

B. Preparation of the Dichlor derivative 


Into a dry vessel provided vuth a mechanical' agitator phos- 
phorus pentacliloride is introduced. The vessel and its contents 
are cooled to — 6° by a refrigerating mixture, the agitator is 
started, and heptanal is introduced little by little, the temperature 
being kept below 0°. 

After all the heptanal has been added, the temperature is 
allowed to rise, and the mass is then heated, stirring all the while, 
until the reaction is completed. It is then cooled and poured 
carefully into ice water. The oxycliloride of phosphorus dissolves 
and decomposes, wMe the dichlor-compound formed is separated 
by decantation, washed until free fi’om acid, dried with anliydrous 
sodium sulphate, and rectified by vacuum distillation under a 
pressm’e of 15 mm. The fraction coming over at 60° to 75° is 

C. Preparation of Heptine 

CH3.(CH2)4.C *: CH. 

Originally, the saponification of the dichlor-derivative formed 
by the preceding operation was effected by the use of alcoholic 
potash (Behai, Bull. Soc. CJiim.., 49, 581, 888), but the 3deld was 
unsatisfactory oving to a molecular transformation, wliich was 
studied by Faworski {BericJite, 20, 781 ; 21, 1614; Kvaft, Jo^lr. 
PraJet. Chem., 2, 37, p. 420) : 

R.OHa.C : CH ^ B.O : CCHg. 

Nowadays, in accordance -with the results of Degrez, the 
saponification is performed by the use of dry pulverised potassium 
hj'^droxide, with the aid of heat and at reduced pressure. 



The resulting product is poured into ice water, separated, 
n-ashcd, dried carefully over anliydrous sodium sulphate, and 
rectitied in a vacuum. The object of this rectification is to free 
the heptine from chlorinated ethylenic hydrocarbons which 
usually accompany it. (A complete separation by rectification is 
difficult, if not impossible.) 

The boiling point of crude heptine is 100° to 100° at 700 mm. 

D. Preparation of Heptine Sodium 

CH 3 .(CH 2 ) 4 .C : CNa. 

The sodium derivative of the hydrocarbon is obtained by the 
following method ; — 

One kilogram of heptine, dissolved in absolutely anh^’drous 
ether, is placed in a reflux apparatus provided with an agitator. 
There is then introduced, little by little, 240 grams of sodium, in 
fine wire, in the cold. The reaction, vigorous at first, slows down 
toward the end, and is brought to completion bj’’ gentle heating 
until the metal disappear.?. 

E. Preparation of the Heptine Carbonate 


The sodium having been entirely dissolved, a quantity of 
anh3'’drous ether is added to the distilling apparatus, so as to 
provide 10 parts of ether to 1 part of the sodium derivative. While 
stirring, there is then added, little by little, 9 parts of methyl 
chlorocarbonate. The mixture is left, while constantlj’’ stirx’ing, 
for several hours, and slight heating is used to completo the 
reaction. It is then cooled and the product decanted, washed 
with water, and distilled through a fractionating column under 
a pressure of 20 mm. The pure product boils at 107° under 20 mm. 

In general, the homologues of methjd heptine carbonate [vert 
dc I'iolctte) are prepared b 3 >- similar methods. This applies to com- 
pounds differing ndth regard either to the acetylenic hj'drocarbon 
from which thej'' are derived or to the radicle which is combined 
with the acid. 

The delicate point in these preparations is the making of the 
lu'drocarbon. The starting material is an aldehyde or a ketone 
which is easily' obtainable, either bj' sjmthesis or bj' some simple 
chemical process from a natural source. 

As examples falling within one or the other of these two classes 
we maj" mention meth\*l isoamjd ketone, which is prepared by the 
controlled decomposition of ethjd isobutylacetate ; methyl hexyl 
ketono, which is formed b}* the oxidation of capr\’lic acid ; method 



lieptyl and methyl nonyl ketones, which exist respectively in 
Algerian and in ordinary commercial oil of rue. 

An important source of further compounds is the undecylenic 
acid which is obtained as' a residual by-product in the manu- 
facture of heptanal, the first stage in the preparation of methyl 
heptine carbonate. This undecylenic acid may be esterified, trans- 
formed into an alcohol by the method of Bouvault and Blanc, and 
thence into an aldeh3’^de which maj'- serve as raw material for 
acetjdenic derivatives of the same number of carbon atoms. 

At the present time certain French houses are marketing the 
following acetylenic esters : — 

Heptine carbonates of methyl and ethyl. 

Octine carbonates of method, ethjd, and amyl. 

Decine carbonates of metl^d and ethyl. 

Undecino carbonate of method. 

The following esters of this series are known : — 



Source from *\v]iich 

ing ester. 

Hoiling point. 


i\Ieth}d }?rop}d ketone . 

Metbyl . 
Isoam3d . 

126°-127° at 24 mm. 
93°- 94° „ 24 „ 
127°-128° „ 22 „ 

Isopeutine . 


Metbyl . 
Isobutyl . 

68°- 69° „ 20 „ 
83°- 84° „ 19 „ 
99°-101° „ 19 „ 


Meth}d butyl ketone . 

Metbyl . 
Etbyl . 

91°- 93° „ 19 „ 
106°-108° „ 84 ., 


Metbyl isoamyl ketone . 

Metbyl . 

98°- 99° „ 19 „ 
110°-112° „ 18 „ 

Heptine . 

Ricinoleic acid . 

Metlayl . 
Isobutyl . 
Isoamyl . 

107° „ 20 „ 
115°-116° „ 17 „ 
126°-127° „ 20 „ 
138°-139° „ 23 „ 
148°-149° „ 20 „ 


Metbyl isoamyl ketone . 

Metbyl . 

98°- 99° „ 18 „ 
110°-112° „ 18 „ 


Metbyl bexyl ketone . 

Metbyl . 
Etbyl. . 
Isoamyl . 

122° ,; 19 „ 
126°-128° „ 16 „ 
145°-148° „ 32 
168°-172° „ 26 „ 

Isooctine . 

Isobexyl metbyl ketone 

Metbyl . 

122°-127° „ 31 „ 
135°-137° „ 30 „ 


Metbylbeptenone . 

Metbyl . 

133°-135° „ 21 „ 
143°-146° „ 21 „ 

Undecino . 

Metbyl nonyl ketone . 

Metbyl , 

168°-172° „ 30 „ 



HEPTYL ACETATE. — ^Tliis ester has a floral-fruity odour. 
Its specific* gravity is 0*S75 ; and hoiling point about 192°. 

HEPTIX ALCOHOL. — ^Tliis alcohol, also knovai as cenanthyl 
alcohol, is methyl-ainyl-carbinol, of the formula CH 3 CH( 0 H). 
CHo.(CH 2 ) 3 .CH 3 . It is a liquid with a. powerful aromatic odour, ' 
and has been found occurring naturally in oil of cloves. It has a 
specific gravity about 0-S32 at 15°, and boils at 175° to 170°. It 
can be prepared from the corresponding aldehj'de, cenanthic 
aldehyde (heptyl aldehyde), bj' melting sodium in diy hot 
toluene, and well stirring until the paidicles arc in a minute state. 
The mixture is then cooled in ice and the aldelyde dissolved in 
acetic acid, and toluene is slowly added^ with continual stirring. 
\^flien the reduction is complete, water is added and the toluene 
layer separated, and the heptyl alcohol purified by fractional 
distillation. Traces of it are used in artificial carnation perfumes. 

HEPTYL ALDEHYDE.— See under Aldehydes, Fatty.” 

HEPTYL FORMATE. — This ester resembles the acetate. 
Its .specific gravity is 0*884: ; and boilmg pomt about 177°. 

CH 3 , is of veiy powerful fruity odom*, and is one of the most 
expensive of recent additions to synthetic perfumery. 

HEPTYX VALERIANATE. — ^This ester has a ver 3 '^ fruity 
odour. Its specific gravity is 0*8775 ; and boiling point about 


HERABOLENE. — ^This bod}” is a tric^’clic sesquiterpene found 
in the essential oil of herabol mjuTh. Von Friedrichs [Arch. dcr. 
PJiarm.. 1907, 245, 208) found it to have the following characters : — 

Boiling point (at 16 mm.) 
Specific gravity at 20 ° 
Optical rotation 
Refractive index 

- 14° 12' 

It 3 -icIds a dihvdrochloride melting at 99°. 

HERACLEUM OILS. — The heracleum oils arc of interest 
in that several of them contain the higher fatty alcohols and their 
estens, substances which have reccntty become so important to 
the up-to-date perfumer. Ilcradcum sjdiondylium is one of the 
umbelliferous plants, loiown as the cow-jiarsnip. The fruit of 



this plant yields from 0-5 to 3 per cent, of essential oil, having 
the following characters : — 

Specific gravity 
Optical rotation 
Refractive index 
Acid value 
Ester value 

. 0-865-0-880 

. 0° to + 2° 

. 1-4260-1-4330 

Zincke {Annalen, 1869, 152, 1) found the oil to consist mainly 
of the caproic and acetic esters of normal octyl alcohol. Moslinger 
{BericJite, 1876, 9, 998) examined two oils in wliich he found 
ethyl butyrate ; a hexyl ester, probably the acetic ester ; octyl 
esters, including the acetate, caproate, caprinate, and laurate. 

Gutzeit {Annale7i, 1872, 163, 193) has examined the oh of 
Hemdeum giganteum, in which he foimd ethyl butyrate. The oil 
of the fruits of this plant has been examined by Sdiimmel da Co. 
{Report, October, 1906, 41 ; April, 1908, 67) and found to have 
the following characters ; — 

Specific gravity 
Optica] rotation 
Refractive index 
Acid value 
Ester value 

Ester value (after acetylation) 

0- 8722-0-8738 
+ 1° to + 1° 14' 

1- 6-3-7 

HERNANDIA OIL. — ^Erom the wood of Eernandia peltata, 
a plant known in Madagascar as faux camplirier , from 1 to 
2 per cent, of an essential oil of powerful cumin odour has been 
obtained. It was examined by Semmler and Zaar {Berichie, 1911, 
44, 815), who found it to contain perilhc aldehyde (dihydro- 
cumic aldehyde), myrtenal, cineol, and hmonene. Sdiimmel dd 
Co, have examined the oil from several parts of the plant, with 
the following results ; {Report, October, 1914 ; April, 1915, 51). 
Eour samples of the trunk wood yielded between 1*03 and 2*06 per 
cent, of oil having the following characters : specific gravity, 
0*958 to 0*963 ; optical rotation, + 83° 45' to + 104° 12' ; and 
refractive index, 1*4969 to 1*6011. Between 75 and 80 per cent, 
of aldehydes were found in the oil. The root wood yielded 0*5 per 
cent, of oil which had a specific gravity 0*9667 ; optical rotation, 
-f- 126° 15' ; and refractive index, 1*5038. It contained 92*6 per 
cent, of aldehydes. The oil distilled from the whole fruits (amount- 
ing to 0*5 per cent.) had a specific gravity 0*963 ; optical rotation, 
-f 50° 16' ; and refractive index, 1*4955. It contained 49 per 
cent, of aldehydes. The almond-shaped kernels yielded 1*38 per 



cent, of oil, of specific gravity 1'004:4 ; optical rotation, -f S7° ; 
refractive index, 1*5061 ; acid number, 7-3 ; and ester number, 

HEXADECYL ALDEHYDE. — ^Tliis body is the normal 16 
carbon aldehyde of the saturated fatty scries, of the formula 
CHt(CH 2 )j^CHO. It is usuall}’ sold as “ Cig aldehyde,” or as 
“ stravberry aldehyde ” on account of its marked odour and 
flavour of ripe stravbcrrics. It is obtained from the methj'l ester 
of palmitic acid by the same process as is undec3'lic acid {q.v) from 
methyl laurate. 

HEXENOL. — ^^Yalbaum [Jour. Prald.Gliem., ii., 06, 191S, 245) 
has found this alcohol, in the form of its phenjdacetic ester, in 
Japanese oil of peppermmt. It is an alcohol, of the formula 
CH3.CH2.CH : CHlCHnlnOH, and has the following characters ; 
specific gravity, 0-8508 ; optical rotation, — 0° 10' ; and refrac- 
tive index, 1-4803. The phenylacetic ester itself, Cj^H^gOo, boils 
at 299°, and has a specific gravity 1-000 ; optical rotation, 0° ; 
and refractive index, 1-4981. 

HEXINE CARBONATES. — See “ Heptine Carbonates.” 

HEXYL ACETATE.— This ester, CH3(CH2)500C.CH3, ocem-s 
m oil of Ilcradcnm giganicum. It is a liquid of fine fruity odour, 
boiling at 170°, and having a specific gravity 0-890 at 0°. 

HEXYL ALCOHOL.— Normal hexyl alcohol CH3(CH2)4CH2 
OH is present in the oils of several species of heracleum, usually 
in the form of liex^d butjTatc. It boils at 157°, and has a specific 
gravity 0-820 at 20°. Isohexjd alcohol is present as its angelic 
acid ester in oil of Roman camomiles. It boils at 154°, and has 
a specific gravity 0-829, and specific rotation -f- 8-2°. 

HEXYL BUTYRATE.— This ester, CH3(CH2)300C(CH2)2. 
CH3 resembles the acetic ester, but has a more powerful fruity 
odour. It is found in several of the heracleum oils, and in the oil 
of Tlicohroma Cacao. 

HEXYL FORIMATE. — ^This ester closety resembles hcptyl 
formate. Its specific gravity is 0‘8S8 ; and boiling point 154°. 

HEXYL VALERIANATE. — This ester closcty resembles the 
corresponding hcptyl ester. Its specific gravitj- is about 0'870 ; 
and boiling point 224°. 

HEXITENIC ALDEHYDE. — See under “ Aldchvdes, 



HIBISCUS ABELMOSCHUS.— See “ Ambrette, Oil of.” 

HINOKI WOOD. — ^TlieHinold tree, Ohaemcecyparis obkisata, 
grows freely in Japan, and thrives exceptionally well in the 
nionntainous districts of Formosa. The wood yields about 
2*4 per cent, of an essential oil with a thujone-like odour. It has 
a specific gravity 0'8S2 ; specific rotation, + 50-37° ; and refrac- 
tive index, 1*4990 at 18*5°. It contains pinene and cadinene, and 
a small quantity of odorous oxygenated constituents not yet 

HOMOHELIOTROPIN. — ^This substance is not a commer- 
cial article, but has been produced in the laboratory as a pale 
yellow oh of agreeable heliotrope odour. It has a specific gravity 
1*265 ; refractive index, 1*5547 at 15° ; and boils at 133° at 8 mm. 
pressm-e. It is prepared by passing ozonised air into a solution of 
safrol m dry acetic acid, and reducing the ozonide so formed bj’ 
means of zinc powder {Jour. Chem. Ind. Japan, 1922, 25, 1409). 

HOMOLINALYL ACETATE.— This ester, of the formula 
CjiHioOOC.CHg, is an oil of sweet bergamot odour, boiling at 
about 115° at 15 mm. It is prepared bj'" the action of homolinalol 
sodium on acetyl chloride. 

HOMORANTHUS OIL. — Homoranilms flavesems is a 
slirub grovsing freely in certain parts of New South Wales. 
Penfold {Jour, and Proc. Roy. Soc. of N.S.W., Ivi., 1923, 197) 
has investigated its essential oil, wliich is of particular interest in 
that it is the only Austrahan essential oil found, so far, to contain 
the olefinic terpene, ocimene, which is present to the extent of 
about 80 per cent. The oil, w^hose earlier fractions have a powerful 
odour of bananas, is yielded to the extent of 0*35 to 0*82 per cent. 
It has the following characters : specific gravity, 0*8206 to 0*8429 ; 
optical rotation, — 1° 75' to + 2° ; refractive index, 1-4836 to 
1*4873 ; saponification value, 8 to 45-9 ; and saponification value 
after acetylation, 51 to 85-4. 

On distillation at 10 mm. tlu’ee crude oils yielded fi’om 81, to 
85 per cent., distilling below’ 77° at 10 mm., wliilst the last two 
consignments gave 16 to 18 per cent., distilling between 123° and 
142° at 10 mm. The first lot gave 11 per cent., distilling betw^een 
72° and 120°, 12 per cent, between 120° and 160°, leaving a 
resinous residue of about 14 per cent., which no doubt partiaU}’’ 
accounts for the high ester and alcohol numbers. 

Determinaiion of d-a-Pinene. — ^Repeated fractional distillation 
at 20 mm., using a six-disc column, of the portion of oil boiling 



below 77° at 10 mm. resulted in the partial separation of a 
small quantity of de.xtrorotator}’’ constituent distilling below 

15 ° 

70°. It had specific gravity at -pr, 0-S313 ; optical rotation 

J. o 

from -f S-7 up to + ; refractive index at 20°, 1*4746. 

It consisted of d-a-pinene together with ocimene, and readily 
gave a nitrosochloride, which on pirrification melted and decom- 
posed at 109°. 

Determivation of Ochncnc. — ^iMany repeated fractional distilla- 
tions conducted at 10 and 20 mm. were made, but it was found 
extremely difficult to remove the associated dextrorotatory 
terpene, indentified as d-a-pinene, despite the high content of 
the olefinic terpene. The best samples separated possessed the 
following characters : — 

Boiling point at 10 mm. 
Boiling point at 20 mm. 


Specific gravity at 


Optical rotation 
Bcfractive index at 20° 




0° to 4- 0 3° 

Its identity was established by the following experiments : — 

(1) The readiness until which it absorbed oxygen when spread 
on a watch glass. Instead of volatilising in the manner of a true 
terpene, it readily yielded a tacky resinous mass, which gave 
highly’ refracting emulsions with alcohol or water. 

(2) On subjecting a sample of boiling point 74° to 75° at 
20 mm. to distillation over sodium at 757 mm., the first drops 
came over at 172°, onc-thii’d of its volume distilling at 173° to 
175°, tlic remaining two-thirds boiling between 175° to 182°, 
thus showing partial conversion into allo-ocimcne. 

(3) On reduction with sodium and alcohol, diliydronnwcene 
was obtained in a moderate^ pine condition, possessing the 
following characters : boiling point, G8° at 20 mm. ; optically 


inactive ; specific gravity at — , 0*790 


refractive index at 

20°, 1*4511. 

(4) The bromide of the above dilnffiromyrccne was prepared 
by dissolving the hydrocarbon in a mixture of 1 part ami'l alcohol 
and 2 parts ether, as recommended in Parr\*’s “ Cheini.stry of 
Essentia! Oils,” vol. ii., page GS. On recrystallising from boiling 
alcohol it melted at 88° to 89°. 

Dctcrminalton of Sesquilcrj}cne. — ^Tlie fractions boiling above 
t- S21 -I 



120° at 10 mm. were redistilled, finally over metallic sodium, 
but the quantity available did not permit of the isolation of the 
sesquiterpene in anything like a condition of purity, with the 
single exception of the last distillation. This was partly accounted 
for by the presence of resinous bodies in the first two lots, which 
is evident from the following table : — 

Boiling point. 

Specific gravit 3 % 



^ index at 




136° Lo 110° at 5 mm. 
127° „ 110° at 5 „ 
133° „ 135° at 10 „ 

0'9192 (17°) 
0-9230 (15°) 

— 7-3° 

— 1-6° 

— 4-25° 




The last mentioned is as pure a sample as was possible to be 

Minor ConstHnents.—^moW quantities of am}*! alcohol and its 
acetic and butyric acid esters were identified. 

HONEYSUCKLE. — The woodbine, of which there are numer- 
ous species, is Loniccrd Pcriclynicnmn (or other species), belonging 
to the natural order Caprifohaccce. It is a favourite climber, 
whose flowers have a delightful fragrance. According to D. 
McDonald (“ Fragrant Flowers and Leaves,” 1895, 71) the following 
are the principal species of lonicera with fragrant flowers : — 

E. pcriclymcnuni, with large creamy flowers, blooming early in 
the year, and with a perfume which is most noticeable in the early 

L. sGrotinum. — This has reddish flowers, blooming late in 
summer and in autumn. 

L. caprifolium. — Tliis is so called because goats are said to be 
fond of its leaves. 

L. JragrcLniissiina, — This plant bears fine white, fragrant flowers 
about February. 

L. hrachypoda . — This is known as Chinese honeysuckle. It bears 
yellow flowers from May to October. 

L. semper vivens.—Y\\\Q is a cultivated ornamental climber 
known as trumpet honeysuckle. 

It is very rare that any preparation of honej’^suckle flowers is 
to be found on the market. The fancy perfumes sold under the 
name honeysuckle are entirely artificial, and do not actually 
reproduce the natural odour. para-Cxesoi derivatives, phenyl- 


PER F u 

acptic aldehyde, linalol, goraniol. storax, and similar mixtnrcs arc 
tised, to %vhicli a floral note is given b}’ the addition of a little 
true Hover oil, such as jasmine, etc. 

HOPS. — ^The hop is IJumithis lupitlus. one of the Canna- 
linacccc. It and its essential oil are used principally for flavouring 
purposes, but very small quantities are occasionally used where 
a special ” note ” in a perfume is required. Hops, which are 
themselves fairly expensive, only yield from O-S to 1 per cent, of 
essential oil, which is very costh'. It contains a sesquiterpene 
which Chapman {Jour. Clicm. Soc., 1903, S3, 505 ;. 1895, 67, 54 
and 780) considers to be a new body and which he termed humu- 
Icne, but which Deussen (Jour. Prald. Clicm., 1911, ii., S3, 483) 
considers to be a niLxture of the isomeric caryophyllenes. Rabak 
(Jour. AgricuK. Research Depi. of Agriculture, Washington, 1914, 2, 
115) has also isolated formic, valerianic, and heptylic acids in the 
free state, and fonnic, acetic, octylic, nonylic, decylic, a;nanth3dic, 
and butyric acids in the form of esters. IMjT'cenol and its esters 
are also j)rosent. Rabak (Zoc. cit.) gives the following as the 
characters of pure hop oils of various origins ; — 








* index. 



. . 



in 94 per 








5'4 vol. 






4 „ 







3-6 „ 

Oregon . 






4-6 „ 







3-3 „ 






3 ,, 

Kew York 







3-5 „ 







3-5 ,, 






3-7 „ 







3-5 „ 





I '5 


3-3 „ 

Saaz (Bohemia) 



0-855 1 




! 4 n 







6 „ 


0-861 ' 



4 „ 

HOUND’S TONGUE. — ^This is the popular name for 
Liairis odoratlsshna, an odorous plant whose leaves contain 
coumarin, growing in the savannahs of North Carolina to Florida. 
(See “ Liatris odoratissima.”) 


21— s 


HOUTTUYNIA CORDATA.— This plant is known in 
Japan as Dohudame, and, according to Shinosaki {Jour. Ghem. 
Ind. Japan, 1921, 24, 557), the whole herb yields, on distillation, 
0*005 per cent, of a brownish essential oil having a specific gravity 
0*8744 ; specific rotation, — 5° ; refractive index, 1*4685 ; acid 
number, 16*65 ; and saponification number, 28*4. It contains 
methyl-nonyl-ketone and an afiphatic terpene, wliich is probably 

HUMULENE. — ^This sesquiterpene {vide “Hops”), which 
may be identical with caryophyllene, v/as isolated from oil of hops 
by Chapman {Jour. Cliem. Soc., 1895, 6*?; 54, 780). It is an oil 
of specific gravity 0*900 at 20°, and boils at 263° to 266°. Deussen 
considers that this sesquiterpene is identical with caryophyllene 
{Jour. Prakt. Ghem., 2, 83, 483). 

HYACINTH. — ^The hyacinth, HyacintJius orientalis, belong- 
ing to the natural order Liliacece, is a native of Syria and other 
districts of western Asia. According to Poucher (“ Perfumes and 
Cosmetics,” p. 222), it was introduced into Great Britain dming 
the sixteenth centurj’-.' It was then only a single-fiowered plant, 
but during the seventeenth century double-flowered plants began 
to appear. The plant is to-day cultivated on a large scale in 
Holland, particularly in the neighbourhood of Haarlem, which is 
one of the principal centres of the Dutch bulb growing industry. 
The odour of hyacinths is sweet and heavy, and if m a confined 
space, often overpowering. The natural perfume is available in 
the form of a concrete or an absolute, but the essential oil is not 
a commercial article (see P. ds E. 0. R., 1912, 77). The perfumes 
of different varieties of the flower vary considerably amongst 
themselves, some types having a rather impleasant odoui’. 
Generally spealdng, the odour of the paler-coloured flowers 
is more deficate than that of the darker varieties, and single 
flowers .usually give a better yield of concrete essence than double 

Enklaar {Ghem. Weekhlad, 1910, 1) obtained a small amount 
of the essential oil by extracting the flowers with benzene, distilling 
ofl the solvent at low pressure, precipitating waxy matter with 
dilute alcohol, and again distilling. The yield was only 0*016 per 
cent, of the weight of the flowers. The oil itself is of rather 
unpleasant odour rmtil heavily diluted. On washing it with 
dilute alkaline solution, traces of sulphuretted hydrogen were 
removed from it. The oil was fractioned at 10 mm. pressme and 



into three fractions : (1) boiling below 90°, (2) boiling 
botv'(,c.’n ‘.'2'' and Q-r^ and (3) boiling from 9i° to 150'’. 

Tiif liivt fraction wn*? found to contain a rcry volatile snb.^tanec 
of di'’grceatilr> odour, which has not been identified. In the 

second fraction a body wa.'^ found, po.-'^ibly of the formula CuITopO, 
having the following characters ; siiecific gravity, 0*907 ; rcfrac- 
tu'C index. 1-40J4 .at 10° ; boiling point, 205° to 20G° (92° to 
94° at 10 mm.) : and optical rotation, -r 1° o2'. Fraction (3) 
was found to contain benzyl benzoate, and probably free benzyl 
alcohol and cinnamic acid esters. Tracc.s of vanillin and freo 
benzoic acid are also probably present. A fluorescent basic 
substance, free from nitrogen, was found, but mcth 3 'l anthranilato 
was absent. The oil contains about 20 per cent, of esters, 1 per 
cent, of free alcohols (benzyl alcohol ?), and 5 per cent, of the 
. fluorescent substance mentioned above. 

TJic majority of the perfumes sold under the name h3'acinth 
to-daj* are cither entirely or almost entireh’ artificial. Into most 
of them several constituents usually enter. Xearlj’’ all of them 
contain a little tcrpineol {q.v.). The following compounds are also 
largely employed : — 

o-Phenylchloreth 5 dene and n-phen 3 d-brometh 3 deno (bromo- 
slyTolcne) *are prepared from cinnamic acid. The former was first 
prepared b 3 '- Stenhouse b 3 ’' distilling cinnamic acid with bleaching 
powder solution.. It is formed b 3 - passing chlorine into a solution 
of cinnamic acid in carbon disulphide and decomposing the phcn 3 d- 
dichloro-propionic acid thus formed by boiling with water. 
<7-Phen3dchloreth3*Ienc boils at 199°. 

Bromost3Tolenc or n-phcn3d-brometh3*lene is formed when 
phcn 3 *ldibromopropionic acid is boiled with water. This acid is 
prepared b 3 ' dissolving cinnamic acid in carbon disulphide and 
gradualh' adding a solution of bromine in carbon disulphide. It 
cr 3 'stallises in plates melting at 195°. On boiling with water, 
a)-bromost3Tolcne is formed, which boils at 219° to 221° and melts 
.at 7°. 

Cinnamic alcohol, formcrl 3 ' called st 3 *ronc, is found in st 3 Tax 
and balsam of Pern. 

It can bo prepared b 3 * Eaponif 3 ’ing cinnam 3 ’I esters with potash 
and steam distilling the product. S 3 'nthcticall 3 ' it is obtained by 
reducing cinnamic ahlch 3 'de. 

It is a cr 3 'stallinc compound when pure, melting at 33° and 
boiling at 25S° ; its specific gravity is 1*010 to 1*030 at 35°. It is 
soluble in dilute alcohol, and can thus be separated from alcohols 


of the geraniol type. On oxidation it yields cinnamic acid melting 
at 133°, and by further oxidation benzoic acid is formed. 

Phenylacetaldeh 3 '’de is the newest, and perhaps the best, of the 
artificial hyacinth odours. It is prepared b}'' heating phenyl-chlor- 
lactic acid with alkalies. When pure, it has a specific gravity of 
1-085, boils at 205° to 207°, and has a refractive index of 1-5253. 

mination of terpenes and sesquiterpenes in terpeneless oils is a 
matter of considerable importance, especially in terpeneless lemon 
and orange oils. The only process which yields at all accurate 
results is that of Bocker {Jour. Praki. Cliem., 1914, ii., 89, 199). 
This will be found described under “ Lemon Oil.” 

HYDROXYCITRONELLAL. — This recently introduced 
synthetic perfume is a mixture of at least two bodies, hydroxy- 
citronellal and diliydroxycitronellal. The commercial article has 
a specific gi’avity about 0-955, optical rotation about -}- 7°, 
refractive index about 1-4530, and boils at about 115° to 135° at 

10 mm. It is of great value in all perfumes of the hly type. 

HYDROXYGOUMARIN.— See “ Umbelliferone.” 

(probably), occurs to theextent of 0-2 percent. inCyprian origanum 

011 (Pickles, Bull. Imp. Inst., 1906, 4, 297). 

HYPNONE. — ^This is another name for acetophenone {q.v.). 

HYPTIS SUAVEOLENS. — ^This is an aromatic plant 
wliich is found from Mexico to southern Brazil, and also in the 
Philippine Islands, Java, Cliina, and the East Indies. The leaves, 
when dried, are sometimes used as an adulterant of patchouli 
leaves, so that the resulting patchouh oil vdll be, pro tanto, 
adulterated with the oil of hyptis. According to Bacon {Philippine 
Jour. Sc., 1909, 4, A, 130), the plant, which is known in the 
Philippines as suheabayog, 3aelds 0-0135 per cent, of a greenish 
essential oil vith an odour of menthol. The natives of Java know 
the plant as daon roeroskee cetan. Menthol appears to be -the chief 
odorous constituent of the oil. Hyqjtis spicaia 3nelds an oil con- 
taining menthone and pulegone {BchimmeVs Report, April, 1904, 
96). Hyptis Salzmamii yields an oil of specific gravity 0-904, 
having a pleasant odour of camomile and balm, and Hyptis 
fasciculata yields one of specific gravity 0-905, having an odour 
of balm and origanum oils. 

HYSSOP, OIL OF. — ^The ordinary hyssop, Hyssopus 



ojricb'.r.lis, is a labiate plant indigenous to the 3Iediten‘ancan 
coun::ic 3 and Central Asia. It grows wild in the hills of 
Danplune and on the plains of Provence. LiJce lavender, it 
prefers chalky hills and dry light soil. It is particularly abundant 
in fhc covs'iovs of La. Fossette a.nd Lo Petour, where it flowers in 
Sepfemoer and October, when it. is gathered for distillation. It 
is also found in the Savoy, Le Bugc}'', Le Cher, and La Nievre. 

Ihc flowers are of a pale colour, varying from blue to white 
and ro.=e, and arc verj* odorous. Apart from its odour value, 
hyssop is esteemed for flavouring purposes, and is said to be an 
ingredient in some of the famous French lirpieurs. 

Hyssop is easily* cultivated, and from 1,500 kg. of the wild herb 
about 7-0 leg. of essential oil are obtained. This is a pleasantly 
aromatic liquid with a sweetish odour. Its characters are as 
follows ; — 

Specific gravity . . . 0-92.5-0-94r5 

Optical rotation . . . — 12° to — 25° 

Refractive index . . . 1-1730-1-4SG0 

Acid value .... 1-2 

Edcr value .... 3-16 

Ester value after acetylation . 35-48 

Jcancard and Satie, however [American Ferf inner. 1909, 4, 84), 
report on two samples distilled in Cannes from the fresh floAvering 
herb, which had the followdng characters : — 

1 . 2 . 

Specific gravity . 



Optical rotation . 

+ 1° 

- 2° 6' 

Acid value 



E'ter value . 



Ester value after acet 3 da- 



According to Gildemeister and Kohler [Wallacli-Fe-stscliriJl 
GoUingen, 1909, 414 ; Schimmel’s Report, April, 1908, 57 ; October, 
1909, 69), oil of hyssop contains jS-pinene, a high-boiling alcohol 
(boiling point, 221° to 222°), and sesquiterpene derivatives. The 
most interesting substance present, however, is a body which has 
been named f-pinocamphone, and which has not been found in 
any other essential oil. This body is present to the extent of 
about 50 per cent, of the oil. It has the following characters ; — 


Boiling point. 

Specific gravity 

Optical rotation 
Refractive index 



0- 9CG2 

— 13° 42' 

1- 4742 



It forms a semicarbazone melting at 228° to 229°, and a 
dibromide melting at 93° to 94°. On reduction it yields a crystal- 
line alcohol melting at 218° and having an odour of camphor. 

Agastaclie pallidijJora, the so-called Great Hyssop, one of the, . 
labiate plants widely distributed throughout the mountainous 
regions of the Far West and Pacific coast of the United States, 
yields an essential oil entirely different from true hyssop oil. 
The following interesting account of this oil is by J. F. Couch. 
(See P. c& E. 0. R., 1922, 177.) 

The material which was used in the following experiments was 
obtained at the experiment station of the Bureau of Animal 
Industry, at Salina, Utah, situated at an altitude of about 
8,000 feet, in the Wasatch Eange. The attention of the investi- 
gator was first directed to this plant by the very intense, fragrant 
odour which diffuses tlu’ough the air in its neighboiu’hood, and 
he describes his experiments with it in the American Journal 
of Pharmacy. Before the blossoms of the plant have opened the 
odour noted resembles that of th-^one ; after blossoming the 
odour is more lilce a mixture of thjune and peppermint. The 
leaves of the plant bruised between the fingers develop a strong 
thyme odour ; the flowering heads subjected to the same treat- 
ment 3 deld an intense peppermint odom with a small thyme 
component. It was therefore thought of interest to investigate 
the essential ofl, of this plant as a possible som’ce of thymol or 

Accordingly several collections of flowering heads and of leaves 
were made 'and the fresh material was immediately, except for 
one experiment, subjected to steam distillation. The quantities 
used and the yields of dry oil were as follows : — 

Per cent. 

July 28. 3,720 grams flowers yielded 6*84 grams oil . 0T84 

Aug. 5. 2,560 grams flowers’yielded 3*96 grams oil . 0T55 

Aug. 11. 3,500 grams flowers 3 deld; d 11-06 grams oil . , 0-316 

Aug. 17. 950 grams leaves jneldcd 0-79 gram oil . 0-083 

The first flowers collected were just beginning to open, and full 
maturity was not attained until about two weeks after, when the 
third lot was collected. This probably accounts for the larger 
yield of oil from the lot of August 11th. The lot of August 5th 
was ground tlirough a meat chopper and allowed to stand over 
night before distilling. Contact with the air turned the ground 
material deep brown, possibly through oxidation of some phenoHc 
gonstituent. The leaves used were carefully separated from ihe 



stems of the plant. These stems are coarse and fibrous, and do 
not appear to contain oil. TIio leaves were then ground through 
the meat chopper and steam dhstilled. 

The oils obtained from the flowers all carried a very pene- 
trating peppermint odour with some marked suggestion of thyme. 
Thej' were slightly j’ellow. The oil from the leaves had a rank 
thyme -odour on!}’. Kone of the samples of oil. nor any of the 
aqueous distillates containing dissolved oil, aflccted ferric chloride 
solution and all were neutral to litmus. 

The following physical constants were determined for the oil 
from the flou’ers : — 

Density at 20° .... 0-91024 

Specific rotatory poAver at 25° . . — 8-60° 

Judex of refraction at 25° . . . 1*4805 

The oil is soluble in the ordinary solvents. On cooling to 
— 10° and letting stand at that temperature for several hours 
there was no separation of anj’- crystalline material. Conse- 
quently, the amount of free menthol, if anj’, present cannot be 
very large. Phenols were tested for b}’’ the usual absorption 
method, using 5 per cent. NaOH. The volume of the oil dimi- 
nished slightly, but on acidifying and shaking out the aqueous 
layer with ether, no phenols Avere found. Pulegone and other 
ketones were tested for and found absent. 

lANTHONE. — ^lanthone, CjcH2.,0, is a ketone of the ionono 
type, resulting from the condensation of citral AA-itli mesit}'! oxide. 
It has a strong Ariolet odour, resembling that of iononc. It boils 
at 101° at 10 mm. pressure. 

The pscudo-ianthone produced in the condensation is an oil 
haA'ing but little odour of violets, boiling at 180° to 185° at 10 mm. 
This is isomcrised to ianthone by dilute sulphuric acid. 

STITUENTS. — It frequcntl}’' becomes of importance to the 
perfumer to examine compounded perfume materials in order to 
obtain ns much information as possible in regard to their com- 
position. Examinations of this nature require a very considerable 
amount of skilled knoAvIcdge and experience, and are often of the 
nature of a prolonged research.- The separation of constituents 
in a mixture of, for example, natural isolates and sj-nthetic per- 
fumes may often be effected by physical method.s, so that the 
determination of the usual con.stants of the separated con'^titnent 



may be sufficient to enable an identification to be made. But 
it is very often necessary to convert the separated constituent 
into one or more of its crystalline compounds, the melting point 
of which enables the original substance to be identified with 
practical certainty. 

The follovdng are examples of typical methods for preparing 
such crystalhne compounds : — 

(1) Hydrocarbon Constituents. — A number of the terpenes form 
characteristic crystalhne derivatives, such as the nitrosochlorides, 
the bromides, and other compounds. 

To prepare the nitrosochlorides, the terpene, or a fraction rich 
in the terpene, is dissolved in tluree times its volume of petroleum 
ether and cooled to 0°. An 8 per cent, solution of nitrosyl chloride, 
in equal volumes of chloroform and petroleum ether, is gradually 
added vdth constant stirring, care being taken that the tempera- 
ture does not rise much above 0°. Alcohol is then added, and the 
crystalline precipitate is separated and recrystallised from warm 
chloroform. Or 5 parts of the terpene, 7 of amyl nitrite, and 12 
of glacial acetic acid are mixed at a temperature of 0° or lower, 
and a mixture of 6 parts of hydrochloric acid and 6 parts of 
glacial acetic acid, also cooled to 0°, gradually added with con- 
stant stirring. Five parts of alcohol are then added, and the 
mixture is allowed to stand in ice and salt for a time, when a 
crystalline mass separates out. Tliis is pm’ified by separation, 
washing with alcohol, drjnng, and recrystaUising from chloroform 
or ether, as may be necessary. 

The bromides of unsaturated terpenes are prepared, e.g., in the 
follo'wing manner. The terpene or terpene fraction is dissolved 
in four times its volume of glacial acetic acid, and the mixture 
cooled in ice. Bromine is then added, drop by drop, so long as it 
becomes immediately decolourised. The mixture is allowed to 
stand until crystals separate. These are filtered off, dried on 
porous paper, and recrystallised from acetic ether. 

(2) Alcohols . — ^The most important crystalline derivatives which 
serve for the identification of alcohols are the phenyl-urethanes 
and the acid phthahc esters. (See also under “ Alcohols.”) 

To prepare the phenyl-urethanes the following method may be 
used. The alcohol is mixed with SO per cent, of its weight of 
phenyl isocyanate, and allowed to stand in a cold place until 
crystallisation has taken place. The crystalline mass is pressed 
between porous paper and recrystallised from petroleum ether or 
ether, as may be necessary. 



The acid phthalic esters may he prepared by mi>dng tlic alcohol 
■noth about an equal -weight of phthalic anhydride and half its 
■w’cight of dry benzene, and heating the mixture under a reflux 
condenser until it becomes homogeneous. This operation should 
proceed for an hour, the temperature being slowly increased up 
to 180° to 190°. 

When the mixture is cold, it is shaken with water and dilute 
solution of caustic soda added until it is very faintly alkaline, 
using phenolphthalein as indicator. The mixture is then extracted 
tu-ice with ether, acidified with dilute sulphuric acid, and the solid 
ester filtered off, dried, and recrystallised from dry benzene. 

( 8 ) Aldehydes and Kcioncs. — ^The oximes, scmicarbazones, and 
phenyl-lmlrazones are the most frequently prepared ciystallino 
compounds of the aldeh 3 'dcs and ketones. For the preparation 
of the oximes equimolccular quantities of the aldehj'de and 
hydroxA-lamine are heated in alcoholic solution on a water bath 
for an hour under a reflux condenser. The hydroxylamine is 
usually added in the form of its hj^drochloride, and liberated by 
means of alkali. For example, 20 grams of camphor are dissolved 
in 50 c.c. of 95 per cent, alcohol, and 15 grams of lydro.xylamine 
lydrochloride added, and then 15 grams of sodium bicarbonate. 
The mixture is heated under a reflux condenser for one to two 
hours, and cooled, diluted ^vith water, and the oxime thus pre- 
cipitated collected, dried, and recr.ystallised from petroleum ether. 

The scmicarbazones arc usuallj’- obtained b 3 ’' dissolving the 
aldclyde or ketone in alcohol and adding an equimolccular mLxturc 
of semicarbazide h 3 ’^drochloride and acetate of sodium. The 
mixture is allowed to stand for a time with occasional shaking, 
and the scmicarbazone is precipitated with water. It is then 
rccr 3 'stallised from hot meth 3 d alcohol. 

The phen 3 ’lliydrazones are usually prepared by acting on the 
aldehyde or ketone with a dilute solution of phenylhydrazine in 
acetic acid. For example, 10 parts of freshly prepared phen 3 l- 
In'drazinc are dissolved in 5 parts of acetic acid, 1 part of the 
aldelyde added, and the whole heated on a water bath for half 
an hour. The mixtmre is allowed to stand for twelve to twcnt. 3 "- 
four hours, when the precipitate is filtered off, dried, and recr 3 -stal- 
liscd from benzene. 

For a number of other useful compounds for identification 
purposes and their preparation, sec “ The Analy.^is of Perfumery 
and riavom-ing S 3 'nthetics and Isolates,” b 3 ' T. H. Durrans 
(P. cO E. 0 . P., 1924, 219). 



IDESIA . — Idesia Poly car pa, also known as Polyearpa Maxi- 
mowiczii, is a large-growing J apanese tree belonging to the Bixinece, 
bearing highly odorous flowers, which are used locally for perfume 
purposes, although the joerfume is not extracted from them. 
Then’ odour is somewhat heavy, but exceedingly sweet, 

ILLURIN BALSAM. — See “ Hardwickia Balsam.” 

distilled from the root of the plant, which is also knoAvn as master- 
wort. It is a plant indigenous to the mountainous regions of 
central and southern Europe. The yield is about 1 per cent, of 
an oil of characteristic aromatic odour, and having a specific 
gravity 0-876 ; optical rotation, + 66° ; and boiling at from 
170° to 190°. Lange (“ Year Book of Pharmacy,” 1912, 100) 
has examined an oil distilled from two-year-old Tyrolese plants, 
which yielded 1 per cent, of essential oil. This oil had the foUowmg 
characters : — 

Specific gravit}^ .... 0-8627 at 20° 

Optical rotation . . . . -j- 59° 30' 

Acid value ..... 0-8 

Ester value . . . . . 17-9 

Ester value after acetylation . . 28-4 

Esters of isobutjnic, isovalerianic, isopropylidene-acetic, formic 
and acetic acids were present, together with terpenes and 

INCENSE. — ^This substance, used for ecclesiastical purposes, 
is a perfume material of considerable antiquity. According to 
Exodus XXX., 34-36, the formula for the substance used in the 
time of Moses for Jewish ceremonial pm'poses is as follows : “ Take 
unto thee sweet spices, stacte, and onycha, and galbanum, these 
sweet spices, with pure frankincense : of each shall there be a like 
weight : And thou shalt make it a perfume, a confection after 
the art of the apothecar}’-, tempered together, pure and holy : - 
And ,thou shalt beat some of it very small and put of it before the 
testimony in the tabernacle of the congregation.” According to 
“ Pharmaceutical Formulas ” (8th ed., p. 228), all these constituents 
are known with the exception of onycha. A lengthy correspondence 
in the Chemist and Druggist, August 26th, 1899, and following 
issues showed that in the Hebrew it seems almost conclusive that 
onycha denotes the crustaceous covering of the shells of certain 
species of univalve shell fish found in the Red Sea and the Indian 
Sea ; but there are also reasons for supposing that a 'high grade 



gum benzoin was the substance in question. E. i\I. Holmes .siated 
that a Jewish recipe for the incense used before the destruction 
of the Temple (incense not now being used iir Jewish ceremonial) 
included as the chief ingi-cdients, balm, onycha, galbanum, frank- 
incense, and in lesser quantities, m^Trh, cassia, spikenard, saffron, 
costus, canella, cinnamon, soap of Carsina, and “ a herb fitted to 
I'aise a fume.” The onj'cha was to be refined In* means of the soap 
of Carsina, and rendered more powerful by digestion in wine of 
Cyprus. It is therefore quite apparent tliat the exact composi- 
tion of the Levitical incense is unknoum, but the following are 
average specimens of the incense used b\' the Roman and Anglican 
cluirches : — 


01ib.anum . .16 

Benzoin . . 11 

Cascarilla bark . l” 
Storax . . 1 


Olibanum . 

. 20 



Cascarilla bark 


Cassia bark 




The principal gum resin xised as the basis of incense is olibanum, 
or frankincense. (See under “ Boswellia Resins.”) In addition 
to this substance, African bdellium is known as African incense. 
(See under “ Bdellium.”) African bdellium is mostly derived 
from Comm'i])ltora ajricana. The tree flourishes in the grassy 
plains of Abyssinia and the Sudan, and is knovm to the natives as 
Oanka. According to Rangon [La Parjumcric Moderne, 1023, 103) 
the bdellium is gathered from December to jMa3\ The natives 
make eight or ten incisions in the trunlc of the tree, and the white 
liquid which exudes soon turns j’cllow, and dries in the form of 
small tears. The}* are then detached with a metal instrument, 
softened by exposure to the sun, and the debris picked out. A 
third gum resin, which is known as incense gum, is the so-called 
incense of India, which is the product of BosicclUa serrafa. (See 
“ Boswellia Resin.”). The incense gum described by Avicenne 
under the name Koondar is sold in the bazaars of the Bombay 
Presidency under the names Dup Salai or Gunda hiroza. 

The frue “incense,” the incense of Arabia, or olibanum, 
although obtained in the main from BosivcUia Cciricrii, al.'jo con- 
tains the product of other species. According to Birdwood and 
Eliickiger, three varieties are to bo distinguished. Of these 
“ Luban Bedowi ” or “ Luban Makur ” is the product of Bostrdlia 
Carlcrii, and is known to the natives as “ ilohr meddu ” {mah 
franl’ivccnsc ; Mohr Madow, Duhan Dakar — see under “ Boswellia 



Resin ”). “ Luban Sheheri ” is the produet of BoswelUa Bhan- 

Dajiana, and is the “ Mohr add ” of the natives. And, lastly, 
“ Luban Mati ” or “ Luban Me3^eti ” is the product of BoswelUa 
Freearana, and is also known as female Jranhincense. 

These native names must be accepted vdth some caution, as 
they are often applied loosely to products whose origin is not 
positively known to the natives. 

In the Antilles and in Guiana exudations from forest trees, such 
as Proiium liepiaphyllum, belonging to the natural order Burse- 
racece, are knorni as incense, but these appear to be elemi or 
tacamahac resins. The white incense is produced by Protium 
hex)iapMjllum and Proiium aliissimum, whilst the so-called Caj’-enne 
incense is produced by Protium guianense. On the west coast of 
Africa several species of Daniellia, giant trees of the Leguminosce, 
are known as incense trees. 

INCHI GRASS OIL. — ^The Indian grass Cymibopogon 
ccesius is closclj’ related to Cymhopogon Martini, but is un- 
doubtedl}'- a different grass. Where the two grasses meet, tran- 
sition forms occur. The essential oil had not been carefully 
investigated until 1922, and as the grass is common in certain 
districts of India and the essential oil is liighl}'- odorous, resembling 
palmarosa oil, it is possible that it ma}’- soon become of commercial 
importance. The following interesting account of the grass and 
oil is due to Moudgill and ICrishna Ij^er (see P. cb E. 0. R., 1922, 
292), and is reproduced fuUj’-, as it has not yet appeared in any 
text-book : — 

Inchippul or Sulclcunarip 2 nil is the vernacular name bj^- which 
the botanical species Gymbojmgon ccesms of Stajjf is known in 
South Travancore. The grass grows wild in profusion on the dry 
hill slopes, and the leaves, when rubbed, give a pleasant aroma 
of ginger. Hence the name mcliippul (gingergrass). The shoots 
appear early after the rains in June, and the grass flowers between 
Oetober and January, when it attains a height of 6 feet or more. 
It then dries up and is invariabty destroj^ed by Are. It may be 
mentioned that the grass occurs in two varieties, one white and 
the other red. The white variety alone was used in this investi- 
gation. It has been observed that the same grass growing in 
moist places or in "waterlogged tracts is almost odourless ; pre- 
sumabl}^ the proportion of essential oil to w^hich the fine aroma is ' 
due decreases in wet lands. 

The existence of an essential oil in this grass seems to have 
been well known ; but the distillation of this grass for its oil, 



reported to have been in practice in former years, lias now been 
entirely given np. Jlcntion is made of this oil bv Parry 
( Ciicinistry of Essential Oils and Artificial Perfumes,’ 1021, 
vol. i.. p. G3) as having been distilled at Arni, in the ^ladras 
Prcsidenc}-, but lie adds that no data arc available about the 
properties of the oil. 

A sample of the oil distilled from this grass in 1920 vas sub- 
mitted by the Department of Industries. Travancore, for analysis 
to Dr. Sudborough, of the Indian Institute of Science, Bangalore, 
and also to the Imperial Institute, London. From a study of the 
constants of the oil Dr. Sudborough (private report) arrived at 
the conclusion that it vas not identical vith any known variot 3 ’’. 
The attention of the authors was drami to this b^^ Mr. I. C. Chacko, 
in charge of the Industries Department, Travancore. At his 
request a more complete investigation was undertaken, particu- 
larly with a view to finding out its value as a perfume oil. While 
tliis paper was in manuscript, a similar report was received from 
the Director of the Imperial Institute, London, who stated that 
the “ inchi ” grass oil differs in its constants from all the grass 
oils of commerce, and that it might be emplojmd as a substitute 
for palmarosa oil, wloich it resembles in odour. 

Our investigation has shown that this oil is quite different in 
character from the oils jdelded by the closely allied varieties 
Cyinhopo^on jlcxuosiis (Cochin lemongrass) and Cyinhopoyoii 
AIoTlnii (the motia and *' sofia ” grasses of western India). 
Both these oils are well known in commerce. Citral and geraniol, 
the valuable constituents of the former and latter oil respectively, 
are both absent in this oil ; while borneol, which has not been 
reported to be present in either of them, appears to be a character- 
istic constituent of the oil from ** inchi ” grass. In addition to 
Z-borneoI, the oil contains Z-camphene, Z-limonene, Z-tcrpineol. and 
sesquiterpene constituents which have not j'ct been identified. 

Si.x hundred pounds of grass consisting of the upper third of 
the plant were collected in October, 1921, and distilled in ah-dried 
condition (moisture = 13 per cent.) with steam in a large copper 
still over a wood fire, the still being provided with a perforated 
false bottom to separate the grass from the water below, and thus 
avoid overheating. The j'ield of the oil was 0-S per cent. (It may 
be mentioned that this still, when used for distilling lemongras.s, 
docs not compare favourably as regards yield with the so-called 
coxintiy still, wliich is invariablj* eraplo 3 'ed for lemongras.s dis' illa- 
tion. Therefore it is believed that the 'above 3 *icld for “ inchi ” 




S ro 

a c3 n 

o w ^ 
u o ^ 

c3 <5^ 

O N 9 9 

^ C<1 rH |> C5 
^ , QO 




O I> T T' 9 

« t- 



P=H^ O 


ra c^ 9 9 

^ r~i KO <Z> 

^ 1 o 

jE2 o 
00 o o > 

6 S > 

i> 6 










1— 1 

lb o 


^ 1 








O o 


o o 


s I 

o io cb 


^ 1 


^ 10. 


CO o o rH 

• CO j> O 

r-^ O 

o fo 
lO lO 

43 ^ 43 

^ ^ d 

O O (D 

O O O 

• O O J> 
-g l> CO CO 

S d d d 

Q .p .p .d 

Ph {>3 

0 ^ ^ 43 

'^.^=3 a 

rcS rO ^ ^ 

it; o o o 

kHDQM 02 


K ® 

O CO . 
^ a 

a ^ 

• rH CJ 

^ s 

4> O c3 

rt +3 ^ 
S cirri 
93 -if IS 
o o S 

PhPh <1 

■ >.c3 

. C/3 O 
<D H 

rd ^ 

. « 


•d d ^ 

5 ^ g 'S 

02<3 Ph 

CD P , O 

^ o 

fcO CZ3 

r d 

^ f-H I— I 


•'^ TT 
rQ fd ^ 

rd <D O 

o d) 2 

CQ 4=> d 


d ^ (D 

-P (n r-1 

P 4> <D 
‘d rd 

H Sh 

^ d S" 

_■ !**• O •/» • VVAAV,*. VJ- V XO u\j 

Btanclarcl conditions ot saponilication were modilied by ns as required by the presence of terpineol. 
(c) Percentage of aldehyde determined by the neutral sulphite method. 


pass, considerable tliongb it is for a grass of this nature, may be 
imploded bj the use of a proper still under different conditions.) 
The oil, when freshly distilled from the grass, has a light crecnish- 
yellow colour, which alters to light brown on keeping.'^ 

The constants of different samjiles of oil olffained from 
different parts of the plant collected at different .stages of its 
growth have been determined, and the result^ tr.bulatcrf for com- 
parison. From these figures it. would appear that tlsc plant 
contains a higher percentage of alcoliol in an c.U'lier stage of 
grov.'tli. and that the flowers yield a larger percentage of iicavior 
oil. tile higher density being due to the presence of a greater 
proportion of the se.'quitorpene fraction. It is intended to 
investigate further the conditions of distillation from the point 
of view of quantity and quality of yield, the numlier of cuttings 
which can be tal.en from the same jffant, and the best season for 

Bcfcn^imifion of AcchjJ F«?nc.— The presence of tcrpincoi in 
the oil found on analysis necessitates an alteration in the usual 
method of saponification. The following optimum conditions 
were found for this oil : A mi.\ture of 10 c.c. of the oil, 12 c.c. of 
acetic anhj'dride, and 2 grams of anh 3 *drous soebum acetate was 
boiled gently on a sand bath for hours. The acetylatcd oil 
was washed and dried, and about 3 grams of it saponified by 
heating on a water bath for 2 hours with 15 c.c. of N/'2 alcoholic 
liotash solution.. 

Fractionation . — ^The oil was fractionated under reduced pressure 
(11 to 13 mm.), and the following fractions obtained ; — 


Loilmg point. 


by volume. 



Colourless . 



no'’-! 35° 

Light 3 'cllow 





Greenish 3 'ellow . 




Pitch-like . 


(b 3 ’ difference) 

The second fraction when cooled gave a large quanti< 3 ' of 
cr\-stals possessing a camphor-IiLc odour. The e were sej.aialed 
In- repeated fractionation and cooling. 

Fraction 1. — This fraction was rcfractioi ated several times 
under ordinary pressure, and finally about equal quantities of the 

r- 337 r: 


fractions A and B were obtained. As the table shows, A resembles 
camphene and B resembles limonene : — 





Boiling point . 





Refractive index 







— 88-1 

— 104 

— 80-8 

— 1C5 



0-8555 at 40° 



A was definitely identified to be Z-campliene by preparing its 
liydi’ochloride, and also by converting it into isoborneol in the 
usual way. An attempt to obtain the sohd h 3 ^drocarbon succeeded 
only partially. An attempt was made to prepare a solid hydro- 
ehloride from B, but it did not succeed. A tetrabromide was, 
however, obtained and identified as Z-limonene tetrabromide. - 

Fraction 2. Identification of the Solid. — It was ciystallised 
several times from petrol and found to melt at 203° to 204°. 
It was identified as borneol by the melting point, boiling point, 
specific rotation, the chloral compound, its p-nitrobenzoatc and 
acid phthalato. Borneol has not been reported to be present in 
any of the similar Cymbopogon oils, and therefore it would seem 
that the essential oil from Gymhopogon ccesius may be charac- 
terised by the presence of tliis alcohol. 

Identification of the Liquid. — The liquid obtained after the 
removal of borneol was redistilled under atmospheric pressure 
with an eight-pear fractionating column, and about 8 per cent, 
jdeld (calculated on the original oil) of a colourless sweet-smelling 
oil possessing the following constants was obtained : — 

Boiling point 







0- 9380 .. 0-933-0-941 

1- 4830 . . 1-4800-1-4840 

— 56-4° . . +100 

The oil was suspected to consist of Z-terpineol. This was 
confirmed by the preparation of dipentene dihydriodide from it 
b^haking with hydriodic acid. 

'^INDOL. — This is a substance of considerable value to the 
perfumer. Closely related to it is the body scatol, and an isomeric 
meth 3 d-indol, which will be conveniently discussed together with 



inclol. Althougli thc^c bodies have very offensive odours in the 
concentrated form, when they are highly diluted they greatly 
improve floral odom'S to which thc\' are adaptable. It is of interest 
to note that the essential oil of jasmin, when extracted direct 
from the flowers, contains no indol and no methyl anthranilatc. 
But if the flowers arc allowed to macerate in cold fat, so that the 
life processes arc allowed to continue in the tissues, more oil is 
developed in the flowens, as the original supph’ passes into the 
fat. In this further supply of essential oil, both indol and methyl 
anthranilatc appear, so that it is probable that these bodies pre- 
existed in the form of glucosidcs, which arc broken down in the 
further biological changes in the plant. The result is that the 
jasmine jjerfume obtained by enfleurage is vastly superior in odour 
to that obtained bj’ e.xtraction with a volatile solvent. It is 
strange that a substance so objectionable in its natural condition 
should be of such great value as a perfume material when diluted. 
It has been discovered in foeccs by Briegor {Jour. Prakl. Chom., 
2, 17, 133), and in the ordinary digestive products by Nencki and 
Kiihne. It is present in enfleurage oil of jasmine, in neroli oil, 
clove flower oil, and the oils of CeJlis reliculosa, Rohinia pseud- 
acacia, Calladium, Miirraya exoiica, and Visnea viocancra. It 
has also been found in the vapours given off in the extraction of 
sugar from molasses. In this case it is accompanied by scatol. 

Indol CsH-N is the mother substance of the indigo group of 
compounds, and was discovered by Bayer in 1SG6 {Annahn, 
140, 4). Although Lipp was actualh’- the first to s3'nthesisc indol, 
bj’ the condensation of sodium ethjdate with amino-chlor- 
styrpleno {Berichie, 1SS4, 17, 10G7), the practical development of 
the chemistry of indol is due almost entueh' to Ba 3 ’er. Indol is a 
ciystalline bod 3 ’ melting at 52° and boiling at 244°. It should onl 3 ’ 
be used in minute quantities in floral combinations, as, if used in 
e.xcess, not onl 3 '' is the perfume ruined, but the indol tends to 
darken in colour, which under certain circumstances is ver 3 ' 

Scivtol is /J-mctlnd-indol, CsITc,N(CHj), and i.s found in ordinary 
civet and' in the e.ssential oil from tlie wood of Celiis reliculosa. 
It forms white cr 3 ’.slals, melting at 95°, and boiling at 205° to 
2GG°. It viclds a Imlrochloride melting at 1G7° to 1GS°, of the 
formula [CsII(;X(Cir 3 )].JICl, and a picric acid com})Ound melting 
at 172° to 173°. It is cqualh' foul-smelling witii indol, aTid 
nia 3 ' bo used in the same manner, but with even greater 



There is an isomeric metli 5 ’’l-indol, Icnorni as methyl-indol-2 or 
metli 3 d-ketol C 8 HglS[(CIl 3 ). This has been prepared by Tischer by 
delwdrating the phenyl-hydrazone of acetone b}'- means of "zinc 
chloride at 180°. The reaction is accompanied bj'' the evolution 
of ammonia. It is a crystalline body melting at 69°, and boiling 
at 268°, and similar to scatol in its general properties. 

Scatol is artificially prepared in a manner similar to that used 
for the preparation of its isomer. The phenjd-hydi’azone of 
propanal CgHg.NH.N ; CH.CH 2 .CH 3 is dehydrated, preferabty by 
means of cuprous chloride. Arbussow and Tichvinskj'’ {Berichte, 
1910) obtained a yield of 60 per cent, of the theoretical in this 
manner. Scatol may be identified by its forming a fine blue 
colour with a solution of dimeth 3 d-amino-benzaldeh 3 ’’de. There 
are numerous methods by which indol can be prepared artificiall 3 ^ 
Most of these, however, are of purel 3 ’' theoretical interest, and onty 
those of some practical importance will be referred to here. To 
obtain indol naturall 3 >', the following process ma 3 ’’ be used. The 
essential oil containing it is mixed with 10 per cent, of picric acid 
and heated to 60°. An excess of petroleum ether is then added. 
A picric acid compound of indol separates out in long red cr 3 ’-stals, 
which are washed vdth petroleum ether and decomposed by 
caustic alkali, the indol thus liberated being dissolved out by 
extraction with ether, and the residue left on evaporation of the 
ether is steam distilled, when pure mdol passes over. This method 
is adapted for a fairly accurate quantitative determination. 
To prepare indol on a satisfactor 3 '’ scale, the following processes 
may be emplo 3 ''ed. It is prepared by the reduction of ortho- 
nitro -cinnamic acid by means of zinc dust. It is prepared to a 
considerable extent as a secondary product during the synthetic 
manufacture of indigo. If anthranilic acid be treated with mono- 
chloracetic acid, phenyl-glycin-or//m-carbonic acid results. B 3 '' 
the careful heatmg of the lime salt of this acid, indoxyl CgH^NO 
results, which b 3 ’' reduction 3 delds indol. Or antliranihc acid is 
condensed with hydrocyanic acid and formaldeh 3 J'de. This results 
in a nitrile CcH 4 (]SrH.CH 2 CN)COOH, which on saponification 
yields the free acid C(,H 4 (NH.CH 2 .COOH)COOH, phen 3 d-glycin- 
ori/io-carhonic acid, which is treated as above described. 

Other processes which have been recommended for the pre- 
paration of indol are those of Berlinerblau (Monatshefic, S, 187) ; 
Thiele and Dimiroth {Berichte, 1895, 13, 1411) ; Vorlander-Apelt 
{Berichte, 1904, 1, 1134) ; Glaud {Jour. Cheiji. 80 c,, 1913, 103, 
1254), and Weermann (German patent 139822). 



In addition to the colour reaction mentioned above for scatol, 
the following colour reactions for indol and scatol may be noted. 
If a few drops of dimethyl-anilme be added to 6 c.c. of a cliloro- 
formic solution containing indol, and a little concentrated sul- 
phuric acid be cautiously added, a pale red colour appears at the 
junction of the liquids, insoluble in chloroform, in the presence of 
indol ; or a violet coloration, soluble in chloroform, in the case of 
scatol. IVith citral instead of dimethyl-aniline, there is a j^ellow 
coloration with indol, and a red coloration with scatol. These 
reactions are sensitive to from 1 in 200,000 to 1 in 500,000. T’inalljq 
if a few drops of an alcohohe solution of vanillin (5 per cent, 
strength) are added to a dilute solution of indol or scatol, and the 
mixture be heated with a slight excess of concentrated hydro- 
chloric acid, an orange -brown colour results in the presence of 
indol, or a violet colour in the presence of scatol. The useful 
table of indol derivatives on p, 341 is due to IMirgodin (in La 
Parfumene Moderno). 

INULA OIL. — The essential oil of Inula viscosa is a pale 
brown hquid of powerful aromatic odour, recalling hyssop and 
eucatyptus. It has the following characters : — 

Specific gravity .... 0*9436 

Optical rotation . . _ 24° 

Scldmmel & Oo. {Report, October, 1903) have reported on an 
oil said to be obtained from this plant, but which had characters 
differing from the above. 

Tliis oil had the following characters : — 

Specific gravity at 25° . . 1*006 

Acid value . . . . .164*6 

Ester value . . . . .15*8 

The plant is widely distributed in Algeria, and is found in the 
Alpes-Maritimes, and is very abundant in the uncultivated lands 
of the Maures and the Esterel. The allied plant, Imila graveohns, 
has an odour of lemons. Its characters are as follows : — 

Specific gravity .... 0*9754 

Oifiical rotation . . . . — 36° 40' 

Refractive index .... 1*4759 

Acid value . 8*45 

Ester value , . . . .161*3 

Ester value after acetylation . . 239*4 

It probably contains bornyl acetate. Inula Eelenium is 



lONONE. — ^Tho discoven,* of the original artificial violet per- 
fume i.-^ one of the outstanding triumphs of modern chemical 
research. This bod}’ vas named ionone by its discoverer, and 
although to-day there are variotis allied derivatives, it will be 
convenient to deal with the whole of the artificial violet compounds 
under this title. 

The -perfume of the violet is one of the most popular of the 
floral odours, but since the actual percentage of odoriferous 
material is so minute, it has never been possible to isolate sufficient 
of the cssejitial oil for a proper investigation to be made. So 
expensive would such an investigation be that Tiemann and 
Kriiger, recognising the similarity between the odours of the 
violet and of orris root (it will be remembered that the old- 
fashioned “ Ariolet powder ” never contained violet perfume, but 
was merely powdered" orris root mixed with starchy matter), 
decided to carry out an investigation on the odorous substances 
of orris root in the hopes that the results would lead them to the 
knowledge of the violet perfume. Whether this has actually been 
the case no one knows, but the results of their work and its further 
development b 3 ’’ others have been so successful that the artificial 
violet perfumes available in consequence are accepted as satis- 
factory’", and it is unlikely that the difficulties attending an 
exhaustive research on the actual violet perfume will be overcome 
for many' years. 

Tiemann and Kriiger, whose results were first published in 1893 
{Berichic, 1893, 26, 2675), worked on orris root, which was 
extracted with ether, the ether recovered, and the residue steam 
distilled in order to ehminate the fixed fatty’- matter, which con- 
sists of resins, irigenin, iridic and myristic acids, etc., whilst the 
volatile portions consist of a little my'ristic acid and its methyl 
ester, oleic acid, oleic anhydride, and the characteristic odour 
bearer, which the discoverers termed irone. It was found that 
this body was a ketone of the formula CijHooO. It is an oil which, 
in the concentrated form, docs not resemble violets, but which, 
on dilution, has a marked resemblance to the violet iicrfume. 
Although it is a ketone, it cannot be succes.sfully' purified by 
means of a bisulphite compound. Such methods as using its 
hydrazone as an intermediary have to be resorted to. Having by 
a prolonged study of irone and its decomposition products ascer- 
tained its constitution, Tiemann and Kriiger set out to synthesise 
it. As a result of these experiments, isomers of irone were obtained , 
which wore at first believed to be but a single body, to which the 



name ionone was given. The resolution of this into its isomers 
followed at a later stage. In the meantime the powerful violet 
odour of ionone was such as to render it unnecessary, at all events 
from a commercial point of view, to follow up the h'one research, 
and for the time being the synthesis of h’one was not achieved. 
This, however, has since been achieved, and an interesting paper 
on the subject was pubhshed by Merling and Welde {Aniialen, 
1909, 119) upon the question. Two parts of ethyl acetoacetate 
and 1 part of acetone arc condensed at — 5° with the aid of 
hydi’ochloric acid. This results in isopropylidene aceto-acetic 
ester (0113)20 : 0(000H3).002.02H5. Tliis ester is then con- 
densed with the sodium compound of ethyl aceto-acetate (German 
Patent 14S0S0 of 1902). The chain is thus closed, and the ethyl 
ester of trimethyl-cyclohexane-carboxyhc acid results. To 100 
parts of this ester 100 parts of phosphorus pentachloride are 
added, the temperature being kept very low. The body is thus 
transformed into the corresponding ester of dichlorcj^clogeranic 
acid, which, by loss of hydrochloric acid, is changed into the ester 
of the monochlor acid, and this, on reduction by sodium, becomes 
saturated by talcmg up 4 atoms of hj^drogen, and from tliis fully 
saturated compound 1 molecule of hydi’ogen chloride is abstracted, 
leaving ethjd- A -4-cyclogeranate . 

This ester is decomposed mto the free acid, which exists in two 
stereoisomeric forms, and which, by Merling’s process, are con- 
verted into the correspondhig aldehj^de. (For details of tliis 
transformation, see La technique industrielle des jiarfums 
synthetiques ” (Paris, 1923, R. Sornet), pp. 86-87.) Irone results 
when the aldehyde so prepared, A-4-cyclocitral, is condensed with 
aeetone. Irene exists in two stereoisomeric forms, a-irone and 
/5-h’one. The mixed body “ irone ” has a powerful violet odom’, 
and has the following characters : — 

Boiling point at 16 mm. . . . 144° 

Specific gravity .... 0*940 

Refractive index .... 1*6011 

Optical rotation .... about + 40° 

Coming back to the initial results of Tiemann, it was found that 
the substance resulting from the condensation of citral and acetone 
in the presence of an aUcah was not irone, but an isomer having a 
powerful violet odour (on dilution), which resulted from the 
following reaction : — 

CioHxcO + (CH 3 ) 2 C 0 = C13H20O -f H2O. 

Citral Aeetone 



As a result of further researches, this body, udheh veas of a 
ketonic nature, u-as named pseudoionono. It was found that, if 
this body ■were lieated with dilute sulphuric acid and a little 
glycerine, it was converted into another isomer, to wliich the 
name ionone was given. This substance is the original iononc of 
commerce, which was sold at a fabulous price in a 10 per cent, 
solution in alcohol. It is now recognised to be a mixture of two 
isomeric ketones. The complete patent specification for this 
body, which ma}' be described as epoch making in the art of 
perfumery, is of sufficient importance to be reproduced tcxtually. 
It reads as follows : — 

“ I, J. C. W. F. Tiemann, member of the firm of Haarmann 
and Reimer, of Holzrainden, residing at Berlin, Germany, do 
hereby declare the natm’e of this invention, and in what 
manner the same is to be performed, to bo particularly described 
and ascertained in and by the following statement : I have 
found that a mixture of citral and acetone, if it is subjected 
in the presence of water for a sufficiently long time to the 
action of hydrates of allraline earths, or of hydrates of alkali 
metals, or of other alkaline agents, is condensed to a ketone 
of the formula C13H00O. This substance, which I term ‘ pseudo- 
iononc,’ may be produced, for instance, in shaking together for 
several days equal parts of citral and acetone with a solution 
of hydrate of barium, and in dissolving the product of this 
reaction in ether. The residue of the ether solution is frac- 
tionally distilled under a reduced pressure and the fraction is 
collected, which boils at a pressure of 12 mm. at a temperature 
of from 138° to 155° C., and from it the unaltered citral and 
unchanged acetone and volatile products of condensation of 
acetone by itself are separated in a current of steam, which 
readily carries oil these bodies. The product of condensation 
remaining in the distilling apparatus is purified b}' fractional 
distillation in vacuo. Under a pressure of 12 mm. a liquid 
distils off at a temperature of from 143° to 145° C. This 
product of condensation of citral with acetone, which I terra 
pseudoionone, is a ketone readilj’^ decomposable by the action ' 
of alkalies. Its formula is Cj^HogO ; its index of refraction, 
Rej = 1"527 ; and its specific weight, 0-904. The pseudoionono 
has a peculiar, but not very .pronounced, odour; it docs not 
combine with bisulphite of sodium ns most of the ketones 
of the higher series, but in other rc.spccts it possesses the 
ordinary characteristic properties of the ketones, forming, in 



particular, products of condensation with plienylhydrazine, 
hydroxylamine, and other substituted ammonias. Although 
the odour of the pseudoionone does not appear to render it 
of great importance for its direct use in perfumery, it is 
capable of serving as raw material for the production 'of 
perfumes, the pseudoionone being eonvefted by the action of 
dilute acids into an isomeric ketone, which I term ionone, and 
which has most valuable properties for perfumery purposes. 
Tliis eonversion may be effected, for example, by heating for 
several hours in an oil bath 20 parts of pseudoionone with 
100 parts of water, 2-5 parts of sulphuric acid, and 100 parts of 
glycerine to the boiling point of the mixture. The product 
resulting from this reaction is dissolved in ether ; the latter is 
evaporated and the residue subjected to fractional distillation 
in vacuo. The fraction distilling under a pressure of 12 mm. 
at a temperatm’e of from 125° to 135° C. is eollected. This 
product may be still further purified by eonverting it, by means 
of phenylliydrazine or other substituted ammonias, into a ketone 
condensation product decomposable under the action of dilute 
acids. The ketone derivatives of the pseudoionone are converted, 
under similar eonditions, into ketone derivatives of the ionone. 
The pure ionone corresponds to the formula CigHgoO, it boils 
under a pressure of 12 mm. at a temperature of about 128° C., 
its specifie weight is 0-935, and its index of refraction is = 1-507. 
The ionone has a fresh flower perfume recalling that of violets and 
vines, and is pecuharly suitable for being used in perfumery, 
confectionery, and distillery. The ionone, when subjected to a 
temperature surpassing 100° C. to the action of hydriodic acid, 
splits off water and gives a hydrocarbon corresponding with the 
formula CigHjg, boiling under a pressure of 12 mm. at a tempera- 
ture from 106° to 112° C. This hydrocarbon is converted by 
strong oxidising agents into an acid of the formula CjoHigOg, 
melting at a temperature of 214° C.” 

Many patents for the production of artificial violet perfume 
have been taken out since the original patent, but the most 
important detail in the chemistry of ionone since then is the dis- 
covery that commercial ionone is actually a mixture of two 
isomeric bodies, which have been termed a-ionone and /9-ionone. 

Pseudoionone has the following characters : — 

Specific gravity at 20° . . . 0-898 

Refractive index at 20° . . . 1-53346 

Boiling point at 12 mm. . . . 143°-145° 



CoPuTucrcial 100 per cent, ionone has, approximately, the 
following characters : — 

33'iiiing point at 10 nim. . . . 12G'-12S° 

Specific gravity at 15° . . . 0'035-0'940' 

Ilefractivc index at 20° . . . 1-5035-1-5070 

Optical rotation . . . .0° 

The characteristic odour of this pure (mixed) ionone is that of 
violets, with a suggC'tion of the odour of vine leaves and blossoms. 
Ticinann {Bcrichte, ISOS, 31, SOS, SG7) .succeeded in resolving this 
substance into a-ionone and ^-ionone. Bj' heating pscudo- 
ionone with dilute sulphuric acid, a diilercnt product is obtained 
from that ;ricldcd when strong sidiJhuric acid is used. In the 
latter case, /?-ionone predominates. a-Ionone is prepared from 
the commercial product by converting it into the crystalline 
oxime, which is reciystallised from petroleum ether, when the 
ketone can be regenerated by the action of dilute sulphuric acid, 
when a-ionone results. This isomer has the following characters : — 

Specific gravity at 15° . . . 0'934 

Refractive index at 20° . . . 1*4990 

Boiling jDoint at 12 mm. . . . 127°-128° 

Jlclting point of oxime . . . 89°-90° 

Melting point of scmicarbazone . 107° 

Slelting point of bromphenylhydrazone 142°-143° 

/9-ionone is obtained from the commercial product by means of 
the scmicarbazone, which crj'stalliscs more readilj’' than the 
corre.sponding derivative of a-ionono, and can thus be separated, 
^-ionone has the following characters : — 

Specific gravity at 15° . . . 0*949 

Boiling point at 12 mm. . . . 134°— 135° 

Refractive index at 20° . . . 1*5198 

Molting point of scmicarbazone . 148°— 149° 

Zilelting point of bromphcnjdhydrazone 11G°-118° 

Lewinsohn (P. cC* E. 0. B., 1923, 259) gives the following account 
of the modem technical method for the manufacture, of ionone ; — 

Contrarj' to the descriptions in the patents and sundry publi- 
cations, the technical preparation of ionone is as follows : The 
process involves two stages : (a) the condensation of lemongrass 
oil with acetone to form pseudoiononc ; (h) the ring-closure or 
cyclisation of pseudoiononc with production of a- and /?-iononc3. 
The German patent (D.R.P. 75120) taken out by Jlcssrs. Haar- 
mann and Reimcr of Hoizminden for the preparation of ionone 
claims the condensation of citral with acetone. The modern 



practice is to use, in place of citral, the lemongrass oil from which 
citral is obtained. This makes the process cheaper, and in no 
way affects the final product. 

{a) ConclGnsaiion . — mixture of equal parts of lemongrass 
oil, acetone, and 10 per cent, caustic soda solution is stirred for 
seventy-two hours in an iron stirring vessel, the temi^erature not 
being allowed to exceed 35°. (In subsequent batches recovered 
acetone ma}^ be used, but the caustic liquor must be more con- 
centrated to allow for the v'ater contained in the acetone.) At the 
end of this time the lower aqueous layer is removed, and the 
upper laj^er is washed several times vuth water. From the 
aqueous laj^er and washings acetone is recovered by distillation. 
The reddish brown oity layer is then distilled in vacuo. Methyl- 
heptenone (formed from the citral) comes over first, and the 
pseudoionone is collected at 135° to 150° at 5 mm. The yield is 
almost quantitative, allowing for the fact that lemongrass oil 
contains only 70 per cent, of citral, a portion of which, as men- 
tioned above, is converted into methylheptenone. 

(6) CycUsaiion . — The cyclisation of pseudoionone requii’es the 
greatest care and skill on the part of the operators. According 
to the concentration of the sulphuric acid used and the tem- 
perature of the reaction, varying mixtures of a- and /5-ionones are 
obtained. Since the former is esteemed more highty and is more 
valuable than the ^ compound, the manufacturer must aim at 
producing the greatest proportion of a-ionone. The use of an 
unsuitable dilution of sulphuric acid results in much unchanged 
pseudoionone and little a-ionone, the main product being /5-ionone. 
On the other hand, if the concentration of the acid be too high 
there is formed, together vdth relatively large amounts of a-ionone, 
much resmous residue, and no pseudoionone is recovered. For 
a maximum yield of a-ionone, therefore, the strength of the acid 
must not be increased unduly. The process here described gives' 
a product containing about 90 per cent, of a- and 10 per cent, of 

One part of pseudoionone prepared as above and 3 parts of 
60 per cent, sulphuric acid are separately cooled to — 8° with 
continuous stirring. The acid is then allowed to run into the 
pseudoionone. A rise in temperature is observed. As soon as 
the thermometer reaches 30° there is seen a sudden change in the 
dark brown colour, which for some moments becomes clearer. 
The mixture is now heated as rapidly as possible to 42°, and at 
once poured upon finely powdered ice. When the ice has melted 



tlie crude iononc floats on the surface as a bro'vvn oil. The acid 
laj-er is removed, and extracted vitli benzene. The extract and 
the crude ionone are united and together washed uith water, 
then with dilute sodium carbonate solution, and finally again 
vdth water. The crude product so obtained is distilled in vacuo, 
the water and terpene b.y-products being removed at 10 to 12 mm., 
and the iononc itself distiUod in a good machine-vacuum at not 
more than 2 to S mm. pressm-e. At this pressure a-ionone 
boils at 11S° to 125°, /S-ionone at lvS0° to 135°. With good 
working there should be no unchanged pscudoiononc. When the 
temperature reaches 135° the distillation is discontinued, and the 
falling of the mereuxy in the gauge is the signal for the empt 3 dng 
of the distillation vessel, since the residue quickl}' sets. With 
well-tramed worlcers the jdeld of distilled ionones is about 40 per 
cent, of the weight of Icmongrass oil used, or 70 per cent, on the 
citral content. The further purification of the ionone so produced 
(wliich is itself a commercial article) to give such brands as 
“ ionone extra ” and “ ionone blanc ” necessitates other, some- 
what delicate, treatments. 

The ionone manufacturer who follows strictly the process 
described above can be sure of alwaj's obtaining a constant 
product, which, enhanced bj’- the addition of a few drops 
of “violet green scent” (or, to give it its chemical name, 
methjd-heptine-carbonate), will find regular purchasers amongst 

Prom the above, it is easily miderstood that pm’e 100 per cent, 
ionone maj'- varj’- considerabl 3 - according to the exact method of 
manufacture, and perfumers must judge ionone on its odour, 
quite apart from its purity. One perfumer ma 3 ’- prefer an ionone 
with less, wliilst another prefers more, /9-ionone in the product. 

It is, moreover, possible to separate the two isomers on a 
commercial scale. (See especiall 3 ’- Tiemami, French Patent 
No. 229G83 ; and Chuit and Bachofen, Bev. Chim. ptir. el applique, 

The hydrosulphonic compound of a-ionone cr 3 ’'stallises more 
readily than the corresponding compound of /?'ionone, wliilst the 
latter is the more easily decomposed b 3 ’’ a current of steam. 

Chuit and Bachofen base their method of separation on the 
relative insolubility of the sodium salt of the hydrosulphonic 
compound of a-ionbne in the presence of sodium chloride, whilst 
the corresponding /5-compound remains in solution. If sodium 
chloride be added to a hot solution of the h 3 '’drosulphonic com- 



pounds, separation of the a-salt takes place slowly as the solution 
cools, and the salt crystallises in fine white scales, which can he 
recrystallised from hot water. The /5-compound remains in 
solution. From the perfumer’s point of view, the complete 
separation of these isomers enables one to produce numerous 
shades of violet perfume, since a-ionone has the sweeter and more 
penetrating odour, whilst /5-ionone, although not so sweet, 
resembles the true violet flower more completely. 

By reducing ionone Skita {Bericlitc, 1912, 45, 3312) has pre- 
pared the corresponding dihydroionones, wliich have odours 
recalling that of cedarwood. Tiemann, however, has prepared a 
dihydroionone apparently isomeric mth the products of Skita by 
the condensation of oitronellal and acetone. The method is, 
generally, identical with that employed in the condensation of 
citral and acetone. Diliydroionone thus produced has a sweet 
odour of fresh flowers. 

A somewhat different shade of odom’ is produced by the use 
of homologues of citral for the condensation. Thus, by using 
methyl-ethyl-ketone — which is a much more difficult and tedious 
condensation than when acetone is used— a methyl-pseudoionone 
results which boils at 160° to 176° at about 20 mm. pressure. 
By cyclisation as in the case of pseudoionone, it yields methyl-' 
ionone boiling at 155° to 160° at 24 mm. pressure. Methyl-ionone 
has an odour somewhat different from that of ionone, and generally 
regarded as superior to the latter. Bm’and, Huguenin, and 
Barbier (French Patent 278338 of September, 1898) have con- • 
densed mesityl oxide, CH3.CO.CH : C(CH3)(CH3), vdth citral at 
the ordinary temperature for fifteen hours, with continual agita- 
tion, in the presence of caustic soda. This results in the formation 
of pseudoianthone, CicHg^O, a liquid boiling at 180° to 185° at 
10 mm. pressure. By cyclisation by means of 65 per cent, sulphuric 
acid in the cold for half an hour, ianthone results. This is a 
highly odorous liquid boiling at 161° at 10 mm. pressure, having 
a violet odour which differs distinctly from that of ionone. 

A body known as cyclo-geraniolidene-acetone has been prepared 
which is, again, another synthetic violet with a characteristic 
shade of odour of its own {Rev. GJiem. Ind., 1904, 141). If sodium 
and carbon dioxide be allowed to act on trimethyl-cyclo-hexanone, 
the corresponding carbonic acid is produced. By the action of 
reducing agents, tliis is transformed into trimethyl-oxy-cyelo- 
hexanone-carbonic acid. If the calcium salt of this acid is dis- 
tilled with calcium formate, cyclo-geraniolidene-aldehyde, CioHjeO. 



results. B}’- condensation •nith acetone, tliis yields cj’-clo-goranioli- 
dene-acelone, wliicli is a mixture of two isomers. In practice, this 
interesting and valuable violet perfume is prepared as follows. 
Pure ether (4,500 parts) is mixed with sodium (98 parts), and 
trimcthjd-cyclo-hexanone (450 parts) added. The mixtme is 
kept under a reflux condenser, and when the sodium is dissolved 
a current of COo is passed through the liquid, which is kept cool, 
to saturation. A gelatinous mass results, which eventually 
crystallises. This is poured on to ice. The ether retains unaltered 
trimethyl-C3''clo-hexanone, whilst bj’’ the addition of a dilute acid 
to the aqueous solution, trimethyl-cj'clo-hexanonc-carbonic acid 
is precipitated. To 100 parts of the sodium salt of this acid 
4,000 parts of sodium amalgam (2 per cent.) are added, the solution 
being dilute and kept cold, A current of COo is passed through 
the liquid. When reaction is complete, dilute sulphuric acid is 
added, and trimcthyl-oxy-c 5 '’clo-hcxanone-carboruc acid is precipi- 
tated. The calcium salts of this acid and of formic acid are then 
distilled in equimolecular quantities in a current of h 3 ’’drogen. 
The resulting cj'-clo-geraniobdene-aldehj’-de is rectified in vacuo, 
and 15 parts of the pure compound (which is a mixture of two 
isomers) ai'c dissolved in 50 parts of acetone, and 0*75 part of 
sodium in 15 parts of absolute alcohol are added, the mixture 
being kept upon ice. The mixture is then neutralised. The a 
and (i ketones thus formed are separated by fractional distillation. 

IMaschmeyer (French Patent 354050 of 1905) has prepared 
methj’l-cj’clo-citrjdidene-methoxy acetate by the condensation of 
citral with methjd chloracctate. The product has a strong violet 

Verlej’- (English Patent 14613, 1897) has prepared a seiies of 
compounds having a %doIet odonr depending on the reaction of an 
acid chloride on C 3 ’’mene in the presence of aluminium chloride. 
Tliis results, for example, in the formation of propion 3 d-c 3 ’myl 
ketone. The ketone is brominated, and the bromo derivative is 
treated with sodium acetate, the acetic ether so obtained having 
an odour of orris root, or violet. 

Hanriot communicated to the Eighth Congress of Applied 
Chemistry (New York, 1912) a characteristic colour reaction for 
the detection of ionone. The ionone is dissolved in concentrated 
hydrocliloric acid. An intense golden yellow coloration is pro- 
duced. If chloral h 3 ^di'ate be added and the liquid be heated, it 
-turns a dirty violet colour. The liquid is allowed to cool and is 
shaken with ether. It is thus decolorised. 



The ethereal solution, when evaporated in the cold on a watch 
glass, deposits a distinct violet colouring matter, soluble in water, 
instantaneously decolorised by ether. This last reaction is so 
delicate that it is sufficient to pour the vapours of ether on to the 
watch glass to produce the dccolorisation of the violet'substance. 

Iso-ionone gives the same reaction. It is even probable that 
this reaction only occurs ^vith ionone after its conversion into 
isoionone by the hydrochloric acid. As a matter of fact, it has 
not been possible to obtain the reaction in a neutral or alkaline 


Neither pseudoionone, nor oil of orris root, nor the natural oO 
of violets gives the reaction, which is sensitive with ionone in 
proportions of 1 in 2,000. It is thus possible to detect the presence 
of ionone in a large number of commercial perfumes. 

The presence of the natural essential oils does not appear to 
interfere vdth the reaction. 

IRALDEINE. — ^This name is that of one of the artificial violet 
perfumes. It is usuallj’ methylionone. (See “ Ionone.”) 

IRIS FLORENTINA.— See “ Orris Root.” 

IRONE.— See “ Ionone.” 

ISOAMYL ALCOHOL. — ^This alcohol, of the formula 
(CH 3 ) 2 .CH(CH 2 ) 20 H, is found in the various eucalyptus oils, and 
also in geranium, lavender, and peppermint oils. It also occurs 
in the form of esters in the oils of Eucalyptus globulus, EucalypUis 
aggregata, and in Roman camomile and cognac oils. It is an 
odorous liquid boiling at 131°, and yields a phenylurethane 
melting at 61° to 62°. 

ISOANETHOL.— See “ Estragol.” 

ISOBORNEOL. — Isoborneol is a stereoisomer of borneol, 
CioHi,OH ig.v.). It closety resembles borneol in general charac- 
ters. It results, together with borneol, on the reduction of the 
ketone, camphor, by means of sodium, or it may be prepared by 
causing the terpene camphene to take up water under the action 
of acetic and sulphiu'ic acids. It ma}?- be prepared in the follo^ving 
manner. One hundred grams of camphene are heated, with 
260 grams of glacial acetic acid and 10 grams of 60 per cent, 
sulphuric acid, to 60° for four hours, the mixture being continually 
shaken. When the reaction is complete, a large amount of water 
is added, when isobornyl acetate (formed by hydration of the 
terpene, accompanied by a molecular rearrangement, and acetyla- 
tion of the so formed isoborneol) results. Excess of free acid is 



waslierl nway witli fl-ater, and the separated ester is saponified in 
the usual manner bj'- saponification under a reflux condenser. 
Tlie^ greater part of the alcohol is distilled off, and the residual 
liquid is poured into a large volume of water. The isoborneol is- 
precipitated, collected on a filter, washed with water, dried on a 
porous plate, and finally rccrj'stallised from petroleum ether. 
The melting point of isoborneol is usually given as 212°, but 
according to Henderson and Heilbron {Proc. Chcm. Soo., 1913, 29, 
381) it is 217°. Its' specific rotation is + 34°. On oxidation 
isoborneol ^fields camphor. It forms a phen}’! -urethane melting 
at 138° to 139°. It can be easily differentiated from borneol by 
the fact that, on heating a solution of isoborneol in benzene for 
an hour "ndth zinc chloride, camphene is obtained. Pure borneol 
under identical conditions remains practically unchanged. 

ISOBORNYL ACETATE.— This ester, CjoHiyOoC.CHg, re- 
sembles bornyl acetate in its sharp fragrant odour. It is an oil - 
of specific gravity 0-9905, and boils at 107° at 13 mm. 

ISOBORNYL FORMATE.— Tliis ester, CioHj-OaC.H, is a 
fragrant oil of specific gravity 1-017 ; it boils at 100° at 14 mm. 

ISOBUTYL ACETATE. — This ester, (CH 3 ) 2 CH.CH 2 . 
COOCH3, '^'hicli has a fruity odour, has a specific gravity about 
0-875, refractive index 1-3920, and boils between 110° and 120°. 
The commercial article is probably a mixture of isomers. 

ISOBUTYL ALCOHOL. — ^This alcohol, of the formula 
(CH3)2CH.CH20H, is found in the distillation waters of Eucalypixis 
(tinygclalinci. It boils at 108° to 109°, and has a specific gravity 
0-8025. Its phenyl-m-ethane melts at 80°. It forms a number 
of highly aromatic esters which are useful in perfumery. 

ISOBUTYL BENZOATE. — This ester, (CH 3 ) 2 CH.CH 2 . 
COO.CgHg, is an oil of very sweet odour, and is often sold as 

EgHntine 100 per cent.” It is used in the manufacture of 
sweet pea perfume. It is an oil of specific gravity 1-006, and 
refractive index 1-4942. It boils at 237° to 238°. 

ISOBUTYL BUTYRATE. — ^This ester has a very fruity 
odour, and as met with in commerce is a mixture of isomers. It 
has a specific gravity about O’SGo, and boils between 152® and 15S®. 

ISO BUTYL FORMATE. — ^This ester, which resem’ Ics the 
acetate, is an oil of specific gravity about 0-890, and boils at 98° 
to 100°. - 


ISOBUTYL PHENYLAGETATE.— This ester, which some- 
times enters into the composition of perfumes known as ” Ideal ” 
and “ Eglantine,” is usually a mixture of isomers. It has a 
specific gravity about 0’990, refractive index I'lSGO, and boils 
at 254°. 

ISOBUTYL PROPIONATE.— This ester resembles the 
acetate, and has a fruity odour. It has a specific gravity about 
0-896, and boils at 137° to 138°. 

ISOBUTYL SALICYLATE.— This ester resembles amyl 
salicylate in odour, and is very useful in the preparation of 
artificial orchid perfumes and in such compositions as irefle. 
It has the formula (CH 3 ) 2 CII.CIl 2 COO.CgH 4 (OII). Its specific 
gravitj'" is about 1-075 ; refractive index, 1-5100 ; and boiling 
point, 259° to 260°. 

ISOBUTYL VALERIANATE. — ^This ester has a very fruity 
odom’. The commercial article is a mixture of isomers having 
the following characters : specific gravitj'- about 0-858 to 0-862 ; 
refractive index, 1-4057 ; and boils from 164° to 170°. 

ISOCARYOPHYLLENE. — ^The scsquitcri^ene mixture iso- 
lated from oil of cloves on the extraction of the eugenol therefrom 
is, in reality, a mixtm’e of two, if not thi-ee, sesquiterpenes. 
Similar mixtures exist in various other essential oils, such as 
pepper, cinnamon, and copaiba oils. {Vide “ Caryophyllene.”) 
Deussen and Lewinsohn {Annalen, 356, 1 ; 359, 245) first showed 
that this was the fact. They separated the clove oil sesquiterpenes 
into two main fractions having the follovnig characters : — 


Boiling point at 16 mm. . 132°-134° 

Specific gravity at 20° . 0-903 

Specific rotation . . — 4-67° 

Refractive index . . 1-4097 



0- 910 
— 23-57° 

1- 4990 

Of these. No. 1 was probably optically inactive, but con- 
taminated with a small amount of optically active sesquiterpene. 
To tliis Deussen gave the name a-car 3 '-ophyllene, and to the 
optically active bod}^ the name |ff-caryoph 3 ^IIene. A thu’d isomer 
was separated, boiling at 124° to 125° at 14 mm., and having a 
specific rotation — 22-22°. This body appears to be identical 
with what'w-as then known as isocaryophyllene, and to it Deussen 
gave the name y-caiyophyllene. Semmler and Mayer {Rerichte, 
44, 3657) agree generally wdth Deussen, but have much comph- 
cated the whole matter by introducing a fresh and emphical 



nomenclature. The}' agree nith Deussen that crude caryoph3dIene 
consists of three distinct individuals. They maintain that 
Deusscn’s a-caryophyllene is identical with Chapman’s humulene, 
isolated from oil of hops (\Tithout, m the writer's opinion, sufficient 
experimental evidence). The two other isomers they suggest 
naming fcj'p-caryophyllene, on account of some relationship the}'’ 
thmk exists with terpinolene, and h‘j?i-caryophyllene, on account 
of a similar relationship with limonene. (For further details of 
this very complicated subject, reference may be made to E. J. 
Parry, “ The Chemistry of Essential Ohs, etc.,” 4th ed., vol. ii., 
pp. S4r-88.) From the perfumer’s point of view, caryophyllene 
may be regarded as the main constituent of the Light oil of cloves 
obtained on extraction of the eugenol, and which is very useful 
in cheap soap perfumery where a clove or carnation perfume is 

ISOESTRAGOL.— See “ Anethol.” 

ISOEUGENOL. — ^Isoeugenol, OioHigOa, is a phenol which is 
found to a very small extent hi nature, but which is of extreme 
importance to the perfumer. It exists in minute quantities in 
the essential oils of ylang-ylang, champaca, and nutmeg. It is, 
however, produced on an enormous’ scale by the isomerisation of 
eugenol (see “ Eugenol ” and “ Carnation ”) as an intermediate 
step in the manufacture of that most important substance, 
vanillin, from oil of cloves. A considerable quantity, however, is 
sold as such to perfumers for the manufacture of artificial carnation 
and similar perfumes. Its odour, being somewhat “ heavy,” 
adapts it to the preparation, when suitably blended, of perfumes 
of the so-called Oriental type. 

Isoeugenol is a pale yellow to colourless oil of powerful clove- 
carnation odour, having the following characters : — 

Boiling point at 760 mm. . . . 263° 

Boiling point at 4 mm. . . . 112° 

Specific gra-vity .... 1-089 

Refractive index . . . . 1-5736 

Optical rotation . . . .0° 

When cooled to a low temperature, isoeugenol solidifies, and 
melts at 34°, but as commercial sp'ecimens invariably contain 
traces of impm'ities, it is always liquid, in a state of superfusion. 
The industrial preparation of isoeugenol is a matter of considerable 
magnitude, and numerous patents have been taken out for its 
manufacture. In the early days of vanillin manufacture the 

356 ' 23-2 


principal difficulty was the fact that in the isomerisation process 
isoeugenol showed a great tendency to give rise to polymerisation 
products and tarry matters. The principal methods which have 
been used are the following. In 1890 Haarmann and Reimer 
(German patent No. 57808) recommended heating the eugenol 
with a satm'ated solution of caustic potash in amyl alcohol. The 
temperature is maintained at 140° for about twenty-four hours. 
The isoeugenol is tlirown out of solution bj'- the addition of a 
dilute acid, and rectified. De Laire (French patent of 1890, 
No. 209149) recommended as an alternative, heating in an auto- 
clave to a temperature of 100° to 100° of a concentrated soffition 
of potassium-eugenol. Kolbe (French patent of 1891, No. 213892) 
preferred an ethyl alcohol solution of caustic potash for isomerisa- 
tion. Einhorn (German patent No. 76982 of April 5th, 1892) 
recommended the use of anhj'-drous caustic potash with eugenol 
at a temperature of 230°. The jneld is proportional to the rapidity 
vdth which the mass is heated to the maximum temperature. 
Schleich (French patent No. 239197 of June, 1924) prefers to heat 
the eugenol with a glycerine solution of caustic potash for six 
hours at about 230°. 

Einhorn’s process is one wliich gives a very satisfactory 3 deld, 
and is ver}'- commonly employed. The oxidation of isoeugenol 
■mil be dealt with under “ Vanillin.” Isoeugenol forms niunerous 
crystalline compounds which serve for its identification. Blono- 
bromisoeugenoldibromide melts at 138° to 139°. If eugenol be 
aeetylated for five hours, acctjd-isoeugenol results, which, if 
dissolved in benzene and precipitated by petroleum ether, melts 
at 79° to 80°. Benzoyl-isoeugenol is prepared by the interaction 
of isoeugenol, benzoyl chloride, and caustic soda. It melts at 
104° to 105°. Isoeugenol also forms a diphenjd-ui'ethane melting 
at 112° to 113°. 

Isoeugenol usually gives the best results when used in con- . 
junction with a little eugenol, the former having a more typical 
carnation odour, and the latter a more typical clove odour. This 
mixtm’e is quite indispensable in the preparation of perfumes of 
the “ ceiUet ” type. 

ISOGERANIOL. — ^This body is an alcohol having a sweet 
rose odour, resulting from enolising eitral with acetic anlij'-dride.’ 
An internal rearrangement of the position of a double bond thus 
takes place, and the acetic ester of ewoZ-citral results. By. the 
reduction of this body by means of sodium amalgam, and methyl 
alcohol slightly acidified -with acetic acid, isogeraniol results. 



Isogeraniol boils at 103° at 9 mm. pressure, and lias a specific 
gravity 0-879 at 20°, and refractive inde.v 1-4730. It forms a 
diplienyluretbane, melting at 73°, and an oily tetrabromide. 

ISOPROPYL ALCOHOL. — Vide “ Alcohol, Isopropyl.” 

ISOPROPYL-o-CRESOL. — ^Tbis is a synonym of earvacrol 
[q.v.). • 

^ ISOSAFROL. — ^This body is the methylene ether of propenyl- 
dioxy-benzene, so it is related to safrol, 'u'hich is the methylene 
ether of aUyl-dioxy-bcnzene, in the same manner as isoeugenol is 
to eugenol. Isosafrol, CioHjo02, is a higlily odorous liquid, having 
a specific gra^vuty l-12o5 ; boiling pomt, 254° ; refractive index, 
1-5780. It is optically inactive. Both safrol and isosafrol jdeld 
heliotropin (g.-y.) on oxidation, but as a much higher yield is 
obtained from isosafrol, the conversion of safrol into isosafrol is 
always a preliminary step in the manufacture of heliotropin. 
Safrol constitutes the principal part of oil of sassafras, but as it 
exists in considerable quantity in camphor oil, the commercial 
supply is derived entirely from the latter oh. Safrol is heated 
for twenty-fonr hours with 2-5 parts of caustic potash and 5 parts 
of 90 per cent, alcohol. At the end of this period an excess of 
water is added, and after recovering the alcohol by distillation, 
the reaction mass is extracted with ether. The isosafrol so 
obtained is dried over calcium chloride and rectified. Variations 
in the methods of isomerisation are similar to those for eugenol. 
{Vide “Isoeugenol.”) Isosafrol is actually a mixture of two 

Hbring and Baum {Berichte, 4S, 3076) have succeeded in 
isolating these two isomerides. _ They have worked vdth the 
isosafrol of commerce, which is a mixture of a- and /3-isosafrol 
with safi’ol. ^-Isosafrol is contained in the fractions of high 
boiling point, from which it may be extracted in the pure state, 
oving to its property of forming a stable picrate, melting at 74°. 

/9-Isesafrol may be separated from the safrol with n’hich it is 
mixed, by the formation of a mercurial compound, which is 
produced by the action of mercuric acetate and calcium cliloride. 

The characters of the two isomerides are as follows : — 


Boiling point (743 mm.) . . 241°-242-5° 

Specific gi-a-vity at 18-5° . . 1-1073 

Refractive index at 18° . . 1-5678 


r JiJ li 1<‘ U IVl E K X 


Boiling point (743 min.) . . 2ol°-251*3° 

►Sjiccific gravity at 17*5° . . 1*1227 

Refractive index at 18° . . 1*5786 

ISOSANTALENE.— Sec " Santalene.^' 

ISOVALERIANIC ALDEHYDE.— This aldehyde, of the 
formula CH 3 .CH(CH 3 )CH 2 .CHO, has been isolated from American 
peppermint oil. It is a volatile liquid, boiling at 92*5°, and having 
a specific gravity 0*804. It forms a thiosemicarbazone melting 
at 53°. 

IVA OIL. — See “ Achillea Moschata.” 

JACINTHS. — = Hyacinth (q.v.). 

JARACANDA. — ^This is a native name for hois de rose {q.v,). ■ 

JASMAL. — See “ Phenyl-gtycol-methjdene-acetal.” 

JASMINE. — ^The perfume of this beautiful flower has always 
been highly esteemed. The flowers are cultivated to a large extent 
in the south of France, the crop beuig gathered almost continuously 
from Juty to October. The jasmine is a member of the natural 
order Oleacece, and is probably a native of India. Donald 
McDonald (“ Fragrant Flowers and Leaves,” 1895, 59) gives the 
follovdng account of the introduction of the jasmine plant into 
Italy, which is probabty only legendary. One of the early Dukes 
of Tuscany was the first o^vner in Italy of a plant, and as he wished 
to retain it as a novelty, he forbade his gardener to give awaj^ any 
cuttings of it. The gardener, however, disobeyed his orders and 
gave his mistress a bunch of, the flowers as a birthday offering. 
She was so pleased vith their perfume that she struck some of 
the branches, and b 3 '' careful cultivation produced large quantities 
of flowers, which she sold to such advantage that she amassed 
a fortune and married the gardener. 

There are about 100 species of jasmine recognised, mostly natives 
of Lidia, Arabia, or Cliina. The species principally cultivated in the 
south of France for the perfume is Jamnimim grandijlorum, the 
so-called Spanish or Catalonian jasmine ; it is usually grafted on 
to cuttings of Ja-sminum officinale. The cuttings are allowed to 
become well developed, and as soon as they are strong enough the 
yellow plants are grafted on, and the plants are left to their 
second j’ear. The flowers are picked as soon as possible after thej' 
open, Avliich is usually in the evening in duty to the middle of 



August, and in the earty morning after that time. The essential 
oil of jasmine is not prepared on a commercial scale, the natural 
jasmine perfume being marketed as an enfleurage or similar pro- 
duct. A ■ver3’’ large amount of the jasmine perfume of commerce, 
however, is partialh* or enthel}^ artificial. 

-The jasmine plant and its perfume has been of considerable value 
in tracing the development of the perfume in the plant tissues. 
Hesse, for example, has shovui that when the flower is extracted 
bj means of a \ olatilo solvent the essential oil does not contain 
either niethj-l anthranilate or indol, whereas when extracted bj? 
the enfleurage process, so that the life processes in the flower can 
continue for some time, there is a prolonged production of essential 
oil due to the decomposition of a glueoside, and not only is a 
laigci yield of essential oil obtained, but both mcthj'l antlmanilate 
and indol api^car as new constituents of the oil, (See also Charabot 
and Gatin, “ La parfum choz la plante,” Paris, 190S). Niviere 
(Bull. SoG. Chim., 1920, 37, SG2) has shovm that if the jasmine 
flov'ers are submitted to a preliminary hych-olj'sis by acids or 
enzjmies before extraction with a volatile solvent, a higher jnold 
of oil is obtained. Mesnard has also used the jasmine flower for 
his investigations { Kccherchcs sur le mode de production du 
parfum dans les fleurs ” : E. Jlesnard, presentee a 1’ Academic par 
Duchartre, Gompics Rendns, 1892, cxv., 282). He states that in 
the jasmine flower, the essential oil is situated in the row of 
epidermal cells on the upper side of the sepals and petals. Some 
exists also in the corre.sponding laj'^er on the under surface, where 
the sepals are colom’cd by a violet pigment. If the evolution of 
the cell contents in flowers at different stages of development be 
foUowed, at first nothing but chlorophjdl is found in the tissues. 
Tannic acid next appears, or glucosides which jdeld tannic acid 
on hj^drolj’^sis. These glucosides also yield the pigments of the 
lowei surface of the sepals. Hydrocliloric acid gas serves as a 
reagent to distinguish between the intermediate compounds 
between the chlorophyll, on the one hand, and the tannic acid, 
pigments, and essential oil on the other. Apparently in the lower 
sm-face, which in the bud state was exposed to the fight and air, 
the intermediate tannoid bodies are slowty oxidised and give rise 
to tannic acid, whilst on the upper surface, being hidden inside 
the bud, these agencies are inoperative, and the same compounds 
are decomposed in a different manner with the production of 
essential oil. 

Jasmine oil obtained from the pomade varies considerabty, 

' 359 


according to the exact method of production. The specific 
gravity may be as low as 0-920 or as high as 1-015. The optical 
rotation lies between — 1° and + 5°, the ester value between 
40 and 72 per cent., calculated as benz 3 d acetate. 

Verley {Comxites Rendtis, 1899, 128, 314 ; Soc. Chiin., 1899, 
iii., 21, 226) investigated the oil extracted from the pomade 
by means of acetone, and stated that the oil consisted of approxi- 
matety 10 per ‘cent, of linalol and 90 per cent, of phenyl -gl 3 ’-col- 
methylene-acetal, which he termed jasmal. The result of this 
work was a French patent for the production of jasmal synthetic- 
alty. Hesse and Muller {Berichie, 1899, 32, 565, 765) showed later 
that tliis bod 3 '- did not exist in jasmine oil. They found then (and 
later, Berichte, 1901, 34, 291) that the oil had the following 

composition : — 

Per cent. 

Benz 3 d acetate . . . . .65 

Linal 3 d acetate ..... 7-5 

Linalol . . . . . .15-5 

Benzo 3 d alcohol ..... 6 

Indol ...... 2-5 

Jasmone . . • . . . -3 

Meth 3 d anthranilate .... 0-5 

Traces of para-cresol and geraniol are also probably present. 
Hesse and Muller {loc. cit.) give the following characters for ten 
samples of oil which they examined : — 




Esters as benzyl 

1 . 


+ 2° 30' 

Per cent. 


2 . 

+ 2° 30' 


3 . 

+ 2° 30' 


4 . 

+ 3° 30' 


5 . 

+ 3° 15' 


6 . 

+ 3° 10' 


7 . 

+ 3° 20' 


8 . 

+ 3° 10' 


9 . 

+ 3° 30' 




+ 3° 20' 


The body jasmone is a ketone of the formula CnHigO, of 
specific gravity 0-945, boiling at 258°' at a pressure of 775 mm. 
It yields an oxime melting at 45°, and a semicarbazone melting at 
201° to 204°. 



The commercial product sold as jasmine oil (apart from the 
absolutes and concretes) is artificial, and is based invariably on 
benzyl acetate, which has a maiked odour of the flower. Some- 
times tliis ester is modified with a little benzyl formate and a little 
linalyl acetate. Tree alcohols, linalol, benzyl alcohol, and traces 
of geraniol are usually present, and traces of benzyl propionate, 
cresylphenj’lacetate, and phenjd-ethyl alcohol are often used. 
A little method antliranilate and indol are generally employed, 
unless an absolutely colourless product is desired, when the indol 
must be omitted. Traces of decyhc aldehj^de, phen 3 dacetic acid, 
and a little natmal jasmine will improve the artificial product 

•Jasminum odoratissimum is a native of Madeira which is 
cultivated in Formosa for the purpose of perfuming tea. The 
yellow flowers, wliich retain their perfume when dried, are known 
as Shuei flowers. 

Er. Tsuchfliashi and S. Tasaki {Jour. Soc. Cliem. Ind., 1919, 38, 
117) have treated these flowers by means of petroleum ether and 
obtained a solid essential oil with a jdeld of 0-277 per cent. This 
solid, exhausted with alcohol, yielded 0-116 per cent, of essential 
oil and 0-T61 per cent, of wax. 

The essential oil thus obtamed is a reddish-brown liquid, vTich 
has the following constants : — 

Specific gravity ..... 0-9309 

Optical rotation . . ... . -j- 5-64° 

Refractive index ..... 1-4845 

Acid value . . . . . . 5-85 

Saponification value .... 92-25 

Saponification value after acetylation . 186-20 

It distils between 60° and 200°, and its composition is as 
follows : 6 per cent, linalol, 6 per cent, linalyl acetate, 1-6 per cent, 
benzyl alcohol, 6 per cent, benzyl acetate, 10 per cent, method 
antlu-anilate and indol. 

Fifty-seven per cent, of the oil is composed of a diterpene and a 
sesquiterpene alcohol, w-hich are found in the fractions with 
high boiling points. The authors found no jasmone in tliis 
essential oil. 

Treatment of the flowers of Jasmimim odoratissimum by 
enfleurage in the cold gave no result. 

J asminum sambac is -a native of Arabia which grows 'wild in 
profusion in India. Its flowers are delightfully fragrant. The 
so-called Tuscan jasmine is Jasminum trifoliatum, knowm in India 



as hadda-mulla. Numerous other species bear very fragrant 
flowers, but their perfume is not extracted. 

J ONQUIL. — ^The jonquil is Narcissus Jonquilla (see “ Nar- 
cissus ”), one of the liighly-scented flowers of the natural order 
Amariillidacece. The natural perfume is extracted b}'' the en- 
fleurage process, and can also be produced as a concrete, but the 
essential oil is not manufactured. Ai’tificial jonquil is very 
similar to artificial narcissus and hyacinth {q.v.). As a rule, 
however, phenyl-ethyl phen 3 dacetate is used in jonquil vdth a 
trace of iDatchouli oil. 

JUNIPER OIL. — Juniper oil is the distillate of the berries of 
Jwiiqjerits communis, one of the Goniferce, growing commonly in 
many jDarts of Europe. The oil is only used to a very limited 
extent in actual perfumery, but is used to a considerable extent 
in the allied industry of flavouring liqueurs and cordials. Jmiiper 
is the basis of all gin flavours. The common juniper is a native 
of Greece, forming a small shrub in most parts of Europe, but 
growing to 30 or 40 feet high in Scandinavia. Schinuncl cb Go. 
give the following as the average ^dcld of oil from juniper berries 
of various origins : — 

Bavarian . 

Per cent. 

Per cent. 

East Prussian . 0-6 

Swedish . . 0-5 

Polish . . 0-9 

Much of the juniper oil of commerce is deprived of its prmcipal 
flavouring ingredients, so that it is really onlj’ a light oil of juniper 
containing little other than terpenes. Juniper oil contains pinene, 
camphene, cadinene, and a small amount of oxygenated con- 
stituents. Amongst these latter is terpinenol and an alcohol not 
yet identified, but having a specific gravity 0-9476 ; ojitical 
rotation, — 4° 30' ; refractive index, 1-4835 ; and boiling point, 
218° to 226°. It is in all jwobabihty a sesquiterpene alcohol. 
Traces of esters are also present. 

Juniper oil is an oil which rapidly oxidises on keeping, vdth the 
formation of insoluble constituents. An oil kept under fair 
average conditions will have the following characters : — 

Specific gravity . .. 
Optical rotation 
Refractive index 
Ester value . . ' . 

Ester value after acetylation 


0- 865-0-890 
— 3° to — 20° 

1- 4750-1-4880 




Occasionally a sample is found to be dextrorotatory to the 
extent of -f- 1° or -p 2°. Samples ■«dth specific gravities above 
0-S90 are usually so old as to be of little flavouring value. 

The essential oil distilled from the berries of .hiniperus jyhcentcea, 
v'hieh is foimd in Sardinia and C\*prus, is higlil}’’ aromatic. It has 
been examiiaed by Puxeddu and Vodret {Gciz. Chim. liah, 1920, 
50, ii., 245—257), vho state that, vhen distilled vith water, the 
macerated berries of the plant yield 2-5 per cent, of essential oil, 
fom’-fifths of this amount distilling over during the first horn, 
wliile the remainder requires about five hours ; the preliminary 
maceration with water should last at least two days. The oil is 
neutral, colourless, and transparent, but turns slightly yellow 
under the influence of light. Its taste resembles that of camphor, 
and it has a marked aromatic odour, while when rubbed between 
the hands it emits the odour of turpentme. It burns until emission 
of dense smoke and resinous odour. It has a specific gravity 
— 0'8G5S at 15° C., and specific rotation -|- 1G"84°. 

K/EMPFERIA ETHEL^^E. — ^The essential oil distilled from 
the tubers of Kmmpferia EtJidcc, a plant belonging to the natural 
order Zingihcraceoi, has been examined by Goulding and Roberts 
{JouT. Clioin. SoG., 1915, 314). The yield was about 2 per cent, 
on the dry material, of an oil having an odour somewhat resembling 
that of neroli oil, with a suggestion of crushed ivy leaves. The oil 
has the following characters : — 

Specific gravity . . . 0-923-0-944 

Optical rotation . . . + 19° 47' to + 30° 4' 

Acid value . . . 1 •0-2-3 

Ester value . . . 5-11-5 

Ester value after acetylation 33-G-47-6 

The dried bulbs, or tubers, which occur in north-eastern 
Transvaal, are there known as Slicnmgulu. 

The composition of the oil is given as follows : — 

_ Per cent. 

Terpenes . . . , , ,21*8 

Cineol ! 17-2 

Ksempferia ketone . . . .13-0 

Alcohols (including linalol) . . . 11.2 

Esters (chiefly methyl anthraniiate) . 1-3 

Phenols •-.... 0-5 

Acids (free) . . . . .0-1 

Residue (chiefly sesquiterpene) . . 34-9 

The ketone present in this oil is a crystalline body, of the 



formula Co^HosOdi melting at 102°, and having a specific rotation 
-}- 198° in cliloroformic solution. In dilute alcoholic solution 
this body has a distinct odour of crushed ivy leaves. It yields 
a hj'droxylaminc oxime meltmg at lSd°, and an oxime melting 
at 106°. 

K/EMPFERIA GALANGA.— The roots of this species of 
Kcem,j)Jcrki yield a heavy essential oil of specific gravity about 
1*025 ; optical rotation, — 10° ; and refractive index, 1*5428. 
It contains ethyl cinnamatc and eth 3 d-^fira-mcthox 3 '-cinnamate. 

KAOLIN. — This substance is used to a small extent in the 
preparation of toilet powders, and also to some extent as a filtering 
powder. It is a white or gre 3 dsh-whitc porcelain cla3^ resulting 
from the decomposition of felspathic rocks, and consists mainl 3 ' 
of one or more silicates of aluminium, with small quantities of 
other inorganic substances. 

KAPUR-KACHRI. — The dried root of Ilcdycliivm spicaium, 
an Oriental plant belonging to the natural order Zivgihcraccce, is 
much valued in the East, cspccialh' b 3 ' the Arabs and Persians, as 
a perfume, and is used b 3 ^ the Hindoos as incense for ceremonial 
purposes. The name (see Sawer, Odorograpliia,” series ii., p. 72) 
is derived from the Grcclv, and means “ sweet show,” in allusion to 
the elegance, fragrance, and whiteness of the flowers of the first 
named species of the genus, Hcdychium coronarium. II. spicatum 
is a native of Sepal and Silhet, and is fairl 3 ^ common in the Punjab 
Himala 3 ’-as. According to D 3 'mock, the dried root forms a con- 
siderable article of commerce in India and China, and is also 
exported to Europe. Two varieties arc Avell recognised, the 
Indian and the Cliinese. Tlic Indian kapur-kachri was formerly 
believed to be identical with the so-called “ lesser galangal root,” 
but this is now known to be incorrect. J. T. Thresh {Pharm. Jour., 
3, XV., 361) describes the odour as intermediate between storax 
and rhubarb root, whilst D 3 miock prefers to sa 3 ’- that it recalls 
that of orris root and camphor. Thresh {loo. cii.) states that the 
amount of actual odoriferous material is vcr 3 ^ small, but that it is 
ver 3 ’- powerful. A minute quantit 3 ’-, exposed to the air, recalls the 
odour of h 3 ’’acinths. He extracted the roots with petroleum ether. 
On allowing the solvent to evaporate slow] 3 ’’, a crop of large, 
colourless, tabular ciystals was obtained, which when recr 3 ^stal- 
lised, melted at 49°. Tliis body appears to be cth 3 d-meth 3 d- 
paracoumarate, but it is not the odoiu’ bearer of the root, which 
has not been isolated and identified. Numerous other species of 



liedycliiiim are cultivated, but liave not been examined to any 
extent, from them perfume point of view. The essential oil of 
Eccli/clii 11771 C07 07i(i7'i7(772 has been found to have a specific gravity 
0-S69, and an optical rotation — 0° 28' {ScUminel cD Co., Berichf, 
April, 1894, 58). A Brazilian j)lant of tliis species was found by 
Peckolt (Pharin. Rv77cl Few York, 1893, 11, 287) to have similar 

KESSO OIL. — ^Ixesso'. oil is the name given to Japanese 
valerian oil, distilled from the roots of Valeria 7 ia offichialis, var. 
angiisiifoha. The jueld is liigh, sometimes reaching as much as 
8 per cent. This (and other valerian oil) is used to a small extent 
in certain soap perfiimes. The Japanese oil has the following 
characters : — 

Specific gravity . . . 0-965-1-000 

Optical rotation . . . _ 20° to — 35° 

Refractive index . . . l-4775-l'4875 

Acid value .... 1-20 

Ester value . . . 90-135 

It has been examined by Bertram and Gildemeister {Arch, der 
Phai'in., 1890, 228, 483). These chemists have identified the 
following bodies in the oil : pinene, camphene, dipentene, ter- 
pineol, borneol, bornyl acetate, bornyl iso valerianate, a sesquiter- 
pene, a blue oil not yet identified, and an ester which has been 
termed kessyl acetate, CJ4H23O.COOCH3. This body is the acetic 
ester of kessyl alcohol, C14H24O2, a crystalline body, melting at 
85°, and boiling at 300° to 302°. The acetate boils at 179° at 
16 mm. pressure, and has an optical rotation — 70° 6'. 

KOBUSHI OIL. — ^The fresh leaves and branches of the 
Kobuslii tree {MagiioUa Koiu-s) yield about 0*45 per cent, of a 
odorous essential oil, of specific gravity about 0-964 ; 
optical rotation, — 1° 6' ; and ester number, 8-9. It has an odour 
of sassafras. The oil contains eugenol, cineol, citral, methyl 
chavicol, and other bodies. The tree flourishes in central Japan. 
(See “Magnolia.”) 

KUNZEA GORIFOLIA. — ^This plant is a very common 
so-called “ tea tree ” growing in the Port Jackson district 
in Australia, and although it . has become less plentiful than 
it used to be, owing to the rapid spread of population, many 
luxuriant patches are still to be found in the neighbourhood 
of Sj dney . The leaves and terminal branchlets yield a very 



fragrant essential oil, whicli lias been investigated bj^ F. R. 
Morrison {Jour, and Proc. Roy. Soc. of N.S.W., 1923, Ivi,, 201). 

A total weight of 387 kg. of leaves and terminal branchlets, cut 
as for commercial distillation, was submitted to distillation •with 
steam and gave an average percentage yield of oil of about 0*35 
per cent., varying from 0-2G to 0-52 per cent. The highest per- 
centage yield was obtained from material collected at Waveiiey, 
on the sea coast, the other localities being some distance there- 

The 3S7 leg. of leaves and terminal branchlets gave on steam 
distillation crude oils possessing physical and chemical character- 
istics as follows : — 


Locality from 
which material 
was obtained. 

Wciftltt of 




Rravlty at 



Pofract Ivc 
index at 


Gore Hill 




+ 18-6° 







-k 12-0° 



LongueviUc > 




-k 24-0° 











-k 25-6° 


Ester no., 

Ester no. 
after acetyla- 
tion. hot 

1^ hourt'. 

E^tor no. 
after acetyla- 
tion. cold 

Z hours. 

Solubility of oil In 80 per cent, 
alcohol (by weight). 



Colour of oil. 



Insoluble in 10 vols. 





Insoluble in 10 vols. 

Dark bromi 




Soluble in 10 vols. 

Light green 




Insoluble in 10 vols. 

Light brown 

The crude oils, on distillation, gave the following results : 
January 27th, 1921, 32 per cent, distilled between 40° and 50° at 
10 mm. ; 5 per cent, between 50° and 100° ; and 54 per cent, 
between 100° and 140°. October 10th, 1921, 36 per cent. distiUed 
below 185° at 762 mm. 

Determination of the Terpene. — ^The lower boiling fraction in 
each case was submitted to repeated distillation, over 80 per 
cent, distilling below 160° at 766 mm. It was found to consist 
principally of d-a-pinene, which gave the following constants : 
January 27th, 1921, boiling point, 155° to 157° ; specific gravity 

— , 0-8613 ; optical rotation, -f- 40-6° ; and refractive index 20°, 

1-4655. October 10th, 1921, boiling point, 155° to 157° ; specific 



gravity 0‘8G23 ; optical rotation, -f- 39"9° ; refractive index 
20°, 1-4C51. 

Confirmatorj^ evidence of its identity vas established by 
preparation of tlie folloving derivatives : — 

^ On acctynt of the high optical rotation the terpene failed to 
give a nitrosochloride ; on mixing, however, with an eqnal 
volume of /ccro-pincne (a)j, - 50-18°, which by itself faded to 
give a nitrosochloi’ide, an excellent 3’iGld of the derivative was 
obtained wliich, Avhen purified, melted at 104°. 

The hydrocliloride, irrepared by saturating 5 c.c. of the' ter- 
pene at — 20° with dry hj’drochloric acid gas, resembled camphor, 
and after recr^ystallisation from alcohol, melted at 127°. 

Oxidation of the Terpene . — 58 c.c. were shaken with 120 grams 
of potassium permanganate, 1,000 c.c. of water, and 500 grams of 
ice until completion of reaction. The liquid was passed through 
a suction filter, whereby the manganese sludge was removed, 
and the cltyr liquid then evaporated to small bullc. It was their 
steam distilled in order to remove unchanged terpene, and again 
concentrated by evaporation. Dilute sulphmic acid was then 
added, the liberated pinonic acid extracted vith chloroform, 
whrj;h latter solvent was distilled off, and the crude acid distiUed 
at 5^ mm. pressure, when the greater portion came over at 180° to 
181 C. After standing for some considerable period crystals 
separated, and these were removed by filtration. On recrystal- 
lisation from petroleum ether the crj-stals melted at 68°; 
0-1704 gram of the pure acid dissolved in 10 c.c. chloroform 
rotated the plane of polarised light -f 1-7°. Specific rotation, 
(a)i, + 100°. The semicarbazone was prepared, and after re- 
crystallisation from alcohol melted at 207° C. The terpene is 
therefore d-a-pmene. ^ 

Deterniination 0/ the Sesquiterpene. — ^That portion of the Gore 
sample of oil distilling between 100° to 140° (principally 
120° to 140°) and the higher boiling portion of the Waverley 
sample were allowed to stand over metallic sodium for a week 
and repeatedty'frtytionated over that metal rmtil a main fractioir 

was obtained, which possessed the follovdng characters ; 

Gore Hill .- boiling point, 129° to 132° at 10 mm.'; specific 

gravity -j— ^ 0-9218 ; optical rotation, -{- 6° ; refractive index 

at 20°, 1-5056. 

Waverley: boiling point, 129° to 132° at 10 mm.; specific 



gravity ’ 0-9239 ; optical rotation, 

refractive index 

at 20°, 1-504G. 

Pre 2 xiralion of ilia Hydrochloride. — Five c.c. of the sesquiterpene 
were dissolved in 10 c.c. of perfectly dry ether, the vessel placed 
in a mixture of ice and salt at — 20°, and the solution saturated 
mth dry hydrochloric acid gas. It was allowed to stand over- 
night, when erystals separated. On recrystallisation from alcohol 
they formed beautiful needles, melting at 116° to 116°; 0-1162 
gram dissolved in 10 c.c. chloroform gave optical rotation 
- 0-65° (a)j, - 39-11°. 

The sesquiterpene which gives a corresponding derivative with 
h 3 ’’drochloric acid gas to that obtained as above, is cadinene, 
which, according to Parry (“ Chemistry of Essential Oils, 2nd ed., 
p. 73) possesses the following eharacters : boiling point, 272° to 
275° at atmospheric pressure ; specific gravity, 0-9215 ; refractive 
index, 1-5065 ; optical rotation, — 105° ; melting point of di- 
hydi’ochloride, 117° to, 118° ; and specific rotation in cliloroform 
solution, — 37°. 

Attempts to prepare the nitroso chloride and nitrosate were 
unsuccessful, but the evidence so far obtained indicates that the 
sesquiterjDene occurring in the oil is probably identical with 

Alcohols. — The saponification values after acetylation of the 
crude oils indicate the presence of fair quantities of alcoholic 
bodies in the oils. The only portion, however, in which these 
bodies appeared to be concentrated was a small fraction boiling 
between 160° to 185°. This fraction was shaken with 50 per 
cent, resorcin solution, and on steam distillation 5 c.c. of a light 
blue oil were obtained which had the characteristic fragrant odour 
possessed to a lesser degree by the crude oil. The constituent 
thus obtained had the follovong characters : specific gravity 

, 0-9029 ; optical rotation, -j- 6-2° ; refractive index at 20°, 



KUROMOJI OIL. — The leaves and young twigs of the 
Japanese plant Lindera sericea, one of the Lauracece, yield an 
essential oU having a very fragrant odour recaUing that of the 
myrtle. The native name for the shrub is Kuro-moji, an allusion 
to the very dark colour of its bark. 

The oil obtainable in commerce is that distilled from the leaves 
and young twigs, and is a dark yellowish oil of powerful balsamic 



odour. It has a specific gravity O-SGO to 0-915, and is usually 
sliglitl}' huvorotatory. It has been investigated by Kwasnik 
{Arch, dll Pharin., 1892, 230, 2G5) and found to contain tf-Iiinonene, 
dipentenc, tcrpineol, and carvone. An oil distilled by ScJiimmel 
cO Co. from similar material was found to contain 9-5 per cent, of 
est-ers calculated as geranjd acetate. Linalol was also detected 
in the oil. Sbinobara has recently bivcstigated this oil. and states 
that it contains 11-4 per cent, of esters, 20 per cent, of free alcohols, 
7-7 per cent, of cineol, 51 per cent, of terpenes, 9-2 per cent, of 
aldeb 3 'des and ketones, and traces of phenols and free acids. The 
free alcohols consist of linalol and geraniol. The oil distilled from 
the remainder of the shrub was also found by Schimmel <£• Co. 
{Boricht, April, 1904, 98 ; 1907, G7) to contain cineol, hnalol, 
geraniol, and geranjd esters. 

LABDANUM. — ^This resinous material is an exceedingly valu- 
able raw material for the perfumer. It has for man\^ 3 ^oars been 
used in the Near East as a fumigating perfume, and has in recent 
3 '^ears become ver 3 ’’ much esteemed as a perfume material in 
western Emrope and America. It is an oleoresinous substance 
obtained from species of Cistiis. In olden days labdanum was very 
lughl 3 ’’ appreciated as a medicament. Its resinous, balsamic, and 
stimulating properties caused it to be used in ailments of the 
stomach and liver, and also as a remedy against loss of hah’. It 
is to-day used, inter alia, as an ingredient in some t 3 ^pes of fumi- 
gating pastilles — pastilles du Serail. The principal species from 
which the oleo-resin is obtained are Cislus ladan ferns and Cistus 
creticus, which are found dispersed all over the island of Cyprus, 
and Cistus monspeliensis, which is found in Greece. Cistus ladani- 
ferus is also found in Portugal and Spain. Several hybrids are also 
knovTi which 3 deld a certain amount of the oleoresin. Formerly 
the oleoresin was collected by the shepherds combing it from the 
fleeces of sheep that had been browsing amongst the cistus 
bushes and so loaded their wool with the sticky exudation. In 
Crete a special instrument is used for collecting the resin which 
is called a ladanisterion, a sort of double rake mth leathern thongs. 
It appears that this method of collecting labdanum does not 
differ materially from that given by Dioscorides in the first 
Century (Tournefort, “ Voyage to the Levant,” i., pp. 56-GO, 
London, 1718). To-day the sheep are not troubled much, and the 
collection is almost entirely by means of- these leather rakes, 
which are used to rub against the 3 munger parts of the plant and 

p- 369 24 


then rubbed in sand to facilitate the removal of the resin. 
Sometimes, also, the branches arc boiled in water and the resin 
skimmed from the surface. The plants yield the oleo-resin most 
freely from May to Juty, and round about noonday is the best 
time for collection. 

Holmes (P. ch E. 0. R., 1911, 155) has shown that Spanish 
labdanum is obtained from Cistus ladanijcrus var. macellaius. 

The botanical characters of the principal Cistus species have ' 
been studied recently b,y A. Camus [Bnllctiii, Roure-Berlrand Fils, 
October, 1920, 3). Labdanum occurs in dark brown to blackish 
viscid masses with a heavy languorous odour recalling the heavj'' 
type of Oriental perfume. It softens on handling, and exhibits a 
grejnsh surface vdien broken, which quickly becomes black on 
exposure to the ah’. It is, of course, insoluble in water, but is 
almost completely'’ soluble in alcohol. It is sometimes adulterated 
with cheaper resins. Very few authentic samjhcs of labdanum 
have been examined, so that the following values must be accepted 
with reserve. Dietcrich (” Analysis of Resins ”) gives the following 
figures : — 





! Saponification 

1 value. 

French commercial 



206-47 • 










German commercial 














Cretan commercial 







E. J. Emanuel' has examined this substance, and gives the 
following as its characters : — 

Per cent. 

Resin extracted by ether . . .48 

Resin by alcohol after ether . . .17 

Essential oil ..... 2 

Ladaniol (guaiol ?) . . . . 0’8 

Gum ....... 3’5 

Mineral matter . . . . .12 

' The most recent and authentic contributions to the know- 



ledge of labdaniim are those of Gcrarclin {Bitll. dcs Sciences 
pliarmacohgiques, 1919, 6, 289), and Gerardin and Gaitefosse {La 
Parjumcrie Moderne, 1920, 6, 111). 

According to Gerardin, labdanum was formerly placed on the 
market in the following forms ; — 

“ In cakes, sticky and blackish lumps. 

“ In small balls, the best coming from Cyprus (Schroder, 
seventeenth century). 

“ In twists or in cord.s. The material, dravm out into rods, was 
twisted into the shape of a ram’s horn, or like tapers (cellar tapers), 
Spanish liquorice, or chewing tobacco. 

" Rolled w^arm, twisted and ornamented with designs (?). This 
peculiarit}’ is met with in Llorelot’s ‘ Dictionnaire des drogues,’ 
1807, and is given by this author only. 

“ In rods or magdaleons. 

“ In bladders, where the material continued to assume con- 
sistence. (Guibourt has thus seen a mass of 12 kg. of fresh and 
soft material, with a peculiar, very strong and balsamic odour.) ” 

Lastly, Poncelet (“ Chymie du gout,” 1755) describes it “ in 
cakes for 'the hard part, in pliials for the liquid (balsam), and in 
leaves of the shrub for the average part with the consistence of 
thick syrup.” 

Tw'o old analyses give labdanum the following compositions : — 

According to Pelletier — Per 

- Resin ...... 20-00 

Gum with a little malate of lime . . 0-60 

Wax ...... 1-90 

Sand, ferruginous .... 72-00 

OU and loss ..... 1-90 

According to Guibourt — Per egnt, 

Resin and oil . *. . . .86-0 

Wax . . . ... . . 7-0 

Aqueous extract . . . . .1-0 

Earthy matter and hairs . . .6-0 

The enormous differences apparent between these two results 
are not surprising, considering the very impure state in which the 
labdanum of commerce is marketed. 

According to Parry (“ Chemistry of Essential OUs,” i., 503), 
the oleo-resin contains 0-7 to 2 per cent, of an essential oil with 
the following characters : — 

Boiling point ' . . . 50°-185° under 15 mm. 

Specific gravity . . . 0-928-1-011 

Ilefractive index . . . 1-5100-1-5140 


i4 ' c 


It oxidises rapidly on being kej)t, and deposits a large quantity 
of crystals. 

According to Masson {Gomptes Rendiis, 1912, 154, 517), this oil 
contains acetophenone and a second ketone of the formula 

CgHigO, whose constants are : — 

Boiling point .... 178°-179° 

Specific gravity at 0° . . . 0-922 

Optical rotation . . . +0° 

Befractive index at 23°. . . 1-4494: 

Melting point of the semicarbazone 220°-221° 

Masson also found in the oil extracted from the oleo-resin sonie 
alcohols, phenols, and esters, while he indicates the probable 
presence of guaiol. 

The ketone CgHjeO is trimelhyl-l,5,5-hexanone-6. 

The substance isolated by Emanuel, of the formula OjyHgoO, 
which he named ladaniol, is, according to Parry, probably an 
impure form of guaiol. 

Rout e- Bertrand Fils have treated a certain quantity of Cistus 
ladaniferus, gathered in the Esterel towards the end of December, 
and obtained, on the one hand, a gum-resin of rather soft con- 
sistence, coloured a deep green, and having a very marked 
balsamic odour, similar to that of the labdanum from Cyprus. 
On the other hand, by simple distillation and vdth a jdeld of 
0-06 per cent., they obtained an essential oil of a golden yellow 

colour, with a very strong and not disagreeable odour. 

The characters of this oil were : — 

Specific gravity at 20° . . . 0-9033 

Optical rotation at 17° . . . •— 12° 10' 

Refractive index at 12-5° . . 1-4800 

Acid value ..... 3-7 

Saponification value . . . 22-37 

Ester value .... 18-67 

Solubility in 90 per cent, alcohol . vol. to 5 vol. 

The distillation waters, exhausted with petroleum ether, gave 
a further 0-02 per cent, of an oil of a deeper colour than the former, 
and whose constants were : — 

Specific gravity’’ at 17-5° . . 0-9755 

Optical rotation at 17° . . . — 2° 40' 

Acid value ..... 18-67 

Saponification value . . . 41-07 

Ester value .... 22-40 

Solubilit}’- in 90 per cent, alcohol . \ vol. and over. 

The latter oil had a much finer odour than the du’ect oil. 



Owing to the small amount of raw material at their disposal, 
they were unable to obtain the oil of Oisiiis inonspcHiansis. Accord- 
ing“ to ScJdmmel <h Go.- {Bericht, October, 1903, p. 81), tliis oU 
has the following constants : — 


Specific gravity at 15° 
Optical rotation . 
Acid value . 

Ester value . 

0'015 per cent. 


-f- 1°40' 



It is of a clear browm colour, and between 20° and 25° deposits 
a considerable proportion of paraffin, melting at 64°. 

LANTANA OILS .—Lantana camara, a plant of the natural 
order Ycvhcnctccoc, is vddely distributed in Java, Hew Caledonia, 
and the Philippines, and grows wild bj’^ the roadside and on waste 
lands tlu’oughout southern India. It is found all over Travancore 
up to an altitude of 4,000 feet. 

According to Moudgill and Vridliachalain (P. cfc E. 0. R., 1922, 
173), the plant has been introduced into India from abroad. The 
essential oil is pale yellow in colour, and has a pleasant aromatic 
odour recalling that of sage. It has been examined by Kanga 
{Journal of the InstiMe of Science, I., ix.), and also by ScJdmmel 
& Co. {Report, October, 1896, and 1909). The most recent examina- 
tion of the oil, however, is that of Moudgill and Vridhachalam 
{loc. ciL). 

Travancore oil 
from leaves. 

Kanga’s figures 
from leaves. 


& Co,'s 

Specific gravity 

(30°/4°) 0-8842 

(24°/24°) 0-92114 



-{- 14-7 

' -j- i"96 

-|- 11-5 

Refractive index 


1-4S93 : 


Acid value 


. — 


Saponification value 




Acetyl value . 




Aldehj'de content . 

2-4 j)er cent. 

. Thc'plant was collected during November. Eour hundred and 
fifty pounds of the air-dried leaves (moisture 12-5 per cent.) were 
steam-distilled in a large copper still with false perforated bottom, 
care being taken that the leaves did not come in contact with the 
hot bottom of the stiU, and a 0-2 per cent, yield of a greenish-yellow 



oil possessing an oclonr "was pleasant and jDersistent, par- 

ticulai’ly ndien considerably diluted "witli alcohol, "svas obtained. 
It showca slight green fluorescence, and was soluble in five or more 
volumes of 07 per cent, alcohol. 

These constants would suggest that the oil consists principally 
of hj’drocarbons, and that it contains very small proportions of 
free alcohol and aldehyde. Further examination bears this out, 
for the oil has been found to be of comparatively simple com- 
position, containing about 10 to 12 per cent, l-a-phellanch’ene, 
SO per cent, of a sesquiterpene much resembling caryophyllene, 
and the rest a complex mixture. 

The oil was fractionated under reduced pressure and, finall 3 q 
three fractions obtained : — 

(1) 55°— 75° at 12 mm. 

(2) 75°-125° at 12 mm. 

(3) 125°— 130° at 12 mm. 


Per cent. 

12 by volume 
8 „ 

74 „ 

6 (calculated by differ- 

Lantana odovata jnelds an oil having an amber odour. It grows 
in J amaica and other islands of the West Indies. 

LARD. — Lard is the purified fat of the hog, Sus scrofa. It is 
used in the extraction of perfumes from flowers by the enfleurage 
process, and is also used in the preparation of various cosmetics. 
Whenever it is used, it is absolutely essential that it should be 
of the very finest quality and free from fatty acids. Further, it 
is important that free fatty acids should not develop in the fat, 
and in order to keep it in good condition it is often digested in 
the melted condition vnth gum benzoin, with constant stirring. 
The fat thus takes up benzoic acid and other constituents from 
the gum, and vill keep sweet for a prolonged period. Lard so 
treated is known as “ benzoated lard ” or adej)s henzoatus. 

Lard, which is produced on a very large scale in the United 
States, is there classified as follows : — 

(1) Neutral Lard No. 1. — ^This is obtained from the fat by 
rendering the finely cut up mass at a temperature not exceeding 
50°. Neutral lard No. 2 is similarly obtained from the fat taken 

, only from the back of the animal. 

(2) Leaf Lard. — ^The residues from which “ neutral lard ” has 
been rendered yield, when subjected to a steam heat in an auto- 
clave, the commercial variety known as leaf lard. 

(3) Choice Kettle-rendered Lard. — ^This is obtained bj’’ rendering 



tlie residues left from the preparation of “ neutral ” lard in open 
steam jacketed vessels. 

(4) Prime Steam Lard . — ^This term is applied to the fat rendered 
from all the other parts of the hog at steam heat. 

Genuine lard for perfumery purposes should be practically 
neutral. It viU generally have characters falling udthin the 
folloudng limits : — 

Melting point . 

Solidifying point 

Saponification value 

Refractomer number 

Iodine value . 

c 100° 

Specific gravity 

Unsaponifiable matter 



49-52 at 40° 



Less than 0-5 per cent. 

It should not contain more than traces of water. Care should 
be used in judging whether a given sample is free from cotton oil 
or not, since the fat of hogs which have been fed on cottonseed 
cake will usually give a slight reaction for cottonseed oil. There 
are a number of fats found in commerce under the name of lard 
substitutes. These are frequently mixtures of a liquid fatty oU. 
with about 20 per cent, of the stearine of beef fat. (For the 
detailed examination of lard, see “ Fatty Foods,” Bolton and 
Ilevis, p. 101.) 

LASERPITIUM OIL. — ^The fruits of a species of Laser- 
pitium, a genus belonging to the natural order UmbelUferoe, yield, 
according to Haensel {Chem. Zentral., 1906, ii., 1496), nearly 
2 per cent, of a dark green essential oil having an odom recalling 
those of aniseed and caraway. It has a specific gravity 0’9538 at ^ 
20° ; acid value, 3*2 ; ester value, 12-3 ; and ester value after 
acetylation, 28-5. It contains limonene, eugenol, diliydroeugenol 
methyl ether, and a paraffin hydrocarbon melting at 57° to 58°. 

LATHYRUS ODORATUS. — ^This plant is the popular sweet 
pea, a member of the natural order Leguminosce. A small amount 
of the natural perfume may be found, but in the main the sweet 
pea perfumes of commerce are synthetic. The essential oil occurs 
in such minute proportions that it has never been systematically 
examined. It certainly contains, however, methyl anthranilate. 
In preparing sjmthetic sweet pea perfumes methyl antlrranilate, 
benzylidene-acetone, hydroxycitroneUal, and terpineol are indis- 
pensable. Numerous other synthetic perfumes are employed, and 


are rounded off with natural essences, such as jasmine and 

LAURIG ALDEHYDE.— See “ Aldehydes, Higher Fatty.” 

LAUREL-LEAF OIL. — Lauriis nobilis, a tree belonging to 
the natural order Laiiracece, possesses leaves having a sharp 
aromatic odour. The oil, which is obtained to the extent of 
from 1 to 3 per cept. from these leaves, has the following 
characters : — 

Specific gravitj’’ 

Optical rotation 
Refractive index 
Acid value 
Ester value 

Ester value after acet 3 da- 
tion . . . , 

0- 915-0-930 (occasional!}’- higher) 
— 15° to — 22° 

1- 4G70-1-4775 



The oil contains pincnc, cineol, linalol, geraniol, 

eugenol, and methyl eugenol. Traces of a sesquiter^mne and a 
sesquiterpene alcohol are also present. 

LAVENDER, OIL OF. — ^As a raw material for the perfumer, 
the essential oil of lavender is certainly amongst the most im- 
portant, both from the j^oints of view of quality and quantity. 
"N^ery large quantities are consumed in the manufacture of that 
t}qDically English toilet perfume, lavender water ; a great deal is 
used in the equally popular eau de Cologne ; and it enters into 
iimumerable other perfume compositions, so that its consumption 
is on a very large scale. France, of com’se, is the home of the 
lavender. A small amount of exceedingly fine quality is grown 
and distilled in England, but for aU practical purposes the world’s 
supply is produced in France. This, of com-se, is not quite so true 
of the spike lavender and its oil, since a considerable amount of 
this oil is produced in Spain. 

So important is this oil to the perfumer, that it is of interest to 
trace the modern vieAvs of experts in reference to the plants from 
which it is actually obtained. 

The position, as conceived by him, is summarised by Lamothe 
(“ Lavand. et Spic.,” 2nd ed., 1908) as follows : — 

The principal lavender species are (1) Lavanchila laiifolia (L. 
spica), also known as spilce lavender, or male lavender. 

(2) Lavandula officinalis {L. vera) also known as the true 
lavender or female lavender. 

(In regard to Lavandula laiifolia, no divergence of opinion is to 
be noted.— E. J. P.) 


Jordan, after a lengthy investigation, considered it necessary 
to classify the true lavender {Lcuvcindula, ojjicinalis) into two 
subdivisions, namely — 

(а) Lavand/ida fragrans {lavande odoraoite ; lavande moyenne). 
Tills variety, he stated, is vddely distributed, occurring at the 
lower altitudes of growth. 

(б) Lavandula Delpliiniensis {petite lavande ; lavande fine). This, 
according to Jordan, is found exclusively in the highest regions 
of growth. 

In addition to these, Lamothe states that there occurs a cross 
between Lavandula fragrans and Lavandula latifolia, which 
Reverchon has named Lavandula Hyhrida, and Chatenier Lavan- 
dula fragrans latifolia (or grosse^ lavande, lavande hdtard, lavendin, 
or spigoure). Distillers, according to Lamothe, recognise these 
varieties under the names (1) Petite lavande, which jnelds the 
finest oil ; (2) Lavande moyenne, which yields' a fine, but less 
valued oil ; and (3) Grosse lavaride, which, being a bastard 
lavender, yields an inferior oil. 

These views have, however, not been entirely accepted by 
Humbert, who in 1919—1920 examined the whole of the lavender 
position for the French Government, and whose considered views 
are the foUowing {vide P. & E. 0. R., 1921, 252). He made very 
extensive tours through the principal lavender districts, and his 
long investigation and journeys have convinced him that Jordan’s 
subdivisions of Lavandula officinalis into two definite varieties is 
incorrect. He is quite satisfied that Lavandula officinalis, Chaix, 
is a specific entity which, although subject to very great variation, 
gives rise in France to only one well-defined geDgraphical race 
the Pyrenean {Lavandula pyrenaica, D.C.). On the other hand, 
very important and interesting, alike from the industrial and 
botanical aspects, is the extreme abundance of hybrids between 
lavender and spike {L. latifolia, Vill.), particularly where the areas 
of the two plants come into contact. The text-books, where they 
do not ignore them altogether, mention these hybrids as excep- 
tional, but the result of careful observation carried out during 
two summers, when natural lavender fields extending over 
hundreds of miles were visited, shows that hybridisation, far from 
being rare, takes place in nature with remarkable facfiity. 

Spike is a native of relatively low altitudes up to 1,000 metres 
when facing south, and no more than 400 metres with a northern 
aspect, while lavender commences, broadly speaking, where spike 
ceases, and attains to 1,500, or even 1,800 metres above sea-level. 



When cither of the two sj^ccies grows distinct from its all}'-, it 
presents a sum of the various distinctive characters (see P. cb 
E. 0. R., June, 1921, pp. 177-178) depending on the extension or 
compression of the inflorescences, the size of the leaves, etc., 
which makes it quite easy of identification. But it is far otber- 
wdse when, ascending from the lower levels to the upper, the 
middle region is reached, where the areas of the two come into 
contact, or even overlap by encroachment ; here are met, often in 
numbers as large as those of the pure si^ecies, plants presenting a 
mixture of characters which forces one to assign to them a hybrid 
origin. Some of the hybrids are easily distinguished, others less 
so (especially' in herbarium specimens) ; these latter have re- 
mained until now almost unlcno-wn to botanists, and it is these 
which present the greatest danger of mixture with the plants 
collected for distillation — for, poor in esters and tainted with 
camphor, they lower considerably the linalyl acetate content of 
the oil, and destroy its fineness ; in fact, they give an essence 
spilce-hke in character. 

A consideration of the -wild plants firmly establishes the specific 
unity of Lavandula officinalis, and if the hybrids -with spilce are 
objectionable from the viewpoint of the quality of the essence, it 
does not necessarity follow, either that lavender cannot be divided 
into strains or cultural races of diverse characteristics, or that 
crossing should, in all cases, be ruled out. On the contrary, it is 
probable that a careful selection may enable the separation of 
important fines, and that reasoned crossing -with spike may 
produce a liigher yield of oil and at the same time maintain a 
satisfactory quality. 

It has been previously shown (P. dh E. 0. R., 1920, p. 253) that 
L. fragrans and L. delpliiniensis, created by Jordan at the expense 
of A. officinalis, cannot be considered as distinct species, but merely 
as two extreme forms of variationJn accord vdth the local condi- 
tions of habitat. Every observation made in the course of last 
summer confirms this -view. In all the mountains -visited, -vdthout 
exception, from the arid chains of Provence to the high Alpine 
valleys, one finds the whole range of variation from one extreme 
to the other ; from the short, squat forms -inth compact inflores- 
cence,’ subsessile flowers, and linear-revolute leaves {fragrans 
corresponding to the most xerophil — i.e., drought-loving — 
adaptation : great dryness of air and soil and intense isolation), 
to the elongated forms with interrupted and tiered inflorescence, 
flowers with distinct pedicels (pedicels sometimes two-fifths of 


P E E F U M-E R Y 

the length of the cah’x), and larger flat leaves {dclphinicnsi-s, the 
form of less arid places). NaUirally, the first predominate on the 
south and on the dr^' crests of the low mountains, where the battle 
against extreme drought induces the morphological modifications 
indicated ; the second to the north or in the Jiigh valleys or 
higher mountains, where mists and rains are less rare, or again 
in the shadow of the forests ; the middle types are found in 
situations of an intermediate character ; moreover, these are the 
most frequent. Further, one can see one type pass into the other, 
following variation in local conditions. 

Thus the Luberon shows, on its arid brows (calcareous, of the 
lower Cretacean system), towards 1,000 metres high, the most 
xerophil forms. But on descending from the summit towards 
the north, one meets on the slopes, less exposed to the sun and 
principally tow^ards the base, where the soil is no longer purely 
calcareous, but a soft Miocene formation and more hygroscopic, 
the whole gamut of transitions to, in the neighbourhood of ponds 
or rivulets, forms presenting the maximum lengthening of axes 
and enlargement of the leaves. The transformation of one form 
to the other can be proved experimentally by planting the seed 
of the xerophil t3q)e — or even by transplanting a growing plant — 
in a damper sofl or climate than the original station, or vice 
versd with the other type. As to the first case, which is the more 
frequent (cultivation in a valley or plain of plants originally 
growing on dry mountains), the morphological modifications are 
much accentuated if the plants are put in a rich soil, and still 
more so if they are treated with manure. Of the same nature are 
the instances where a fall' of rubbish has, by chance, brought 
about the layering of some shoots of a xerophil lavender : the 
layered branches may show larger leaves and tiered floral glo- 
merules. Finally, stocks of the same type after being burnt down, 
give forth the following year very vigorous branches, vdth large 
leaves and floral glomerules very spaced out by the elongation of 
the internodes. The cause of this variation is very simple. The 
first shoots which forin after the fire are few in number ; thus they 
receive all the sap absorbed by the full uninjured root system, 
and at the same time the loss of water by transpiration and 
chlorovaporisation is temporarily reduced or suppressed. Hence 
everything occurs as if the plant grew in a humid situation — it 
loses the characteristics adapted to dryness j the leaves enlarge, 
the internodes become elongated. These first 'shoots are very 
strong ; the ashes derived from the fire also contribute to their 



vigour Iby fertilising the soil. During the following years the 
shoots multiply, the original conditions tend to return, and the 
xerophil characters reappear progressively. 

When the original diagnoses of the two Jordanian species are 
compared, one is struck by the fact that the characters on which 
the author based them distinction are precisely -those which are 
easily brought about by change of conditions, and, besides this, 
they are merely quantitative characters. Jordan’s own words 
relative to L. fmgrans are: Its appearance is very different 
(from that of L. clel'phiniensis) ; it forms denser clu